Desnicotinyl indinavir

Base Information

• Chemical Name: Desnicotinyl indinavir
• CAS No.: 150323-38-9
• Molecular Formula: C30H42 N4 O4
• Molecular Weight: 522.688
• UNII: 98N2VRY18Z
• Nikkaji Number: J626.215E
• Wikidata: Q27272128
• ChEMBL ID: CHEMBL949
• Mol file: 150323-38-9.mol

Synonyms:150323-38-9;Desnicotinyl indinavir;(+)-Desnicotinyl indinavir;CHEMBL949;UNII-98N2VRY18Z;98N2VRY18Z;(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-5-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-5-oxopentyl]-N-tert-butylpiperazine-2-carboxamide;Indinavir sulfate specified impurity B [EP];Des-3-pyridylmethyl Indinavir (>90per cent);(2S)-1-((2S,4R)-4-Benzyl-2-hydroxy-5-(((1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)amino)-5-oxopentyl)-N-(1,1-dimethylethyl)piperazine-2-carboxamide;(S)-1-((2S,4R)-4-Benzyl-2-hydroxy-5-((1S,2R)-2-hydroxyindan-1-ylamino)-5-oxopentyl)-N-tert-butylpiperazine-2-carboxamide;D-Erythro-pentonamide, 2,3,5-trideoxy-N-((1S,2R)-2,3-dihydro-2-hydroxy-1H-inden-1-yl)-5-((2S)-2-(((1,1-dimethylethyl)amino)carbonyl)-1-piperazinyl)-2-(phenylmethyl)-;D-Erythro-pentonamide, 2,3,5-trideoxy-N-(2,3-dihydro-2-hydroxy-1H-inden-1-yl)-5-(2-(((1,1-dimethylethyl)amino)carbonyl)-1-piperazinyl)-2-(phenylmethyl)-, (1(1S,2R),5(S))-;Des-3-pyridylmethyl Indinavir;Indinavir sulfate impurity, desnicotinyl indinavir- [USP];D-erythro-Pentonamide, 2,3,5-trideoxy-N-[(1S,2R)-2,3-dihydro-2-hydroxy-1H-inden-1-yl]-5-[(2S)-2-[[(1,1-dimethylethyl)amino]carbonyl]-1-piperazinyl]-2-(phenylmethyl)-;INDINAVIR METABOLITE M6;SCHEMBL9251639;BDBM50287657;AKOS030241857;Des-3-pyridylmethyl Indinavir (>90%);INDINAVIR SULFATE IMPURITY B [EP IMPURITY];Q27272128;INDINAVIR SULFATE IMPURITY, DESNICOTINYL INDINAVIR- [USP IMPURITY];(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-5-[[(1S,2R)-2-hydroxyindan-1-yl]amino]-5-oxo-pentyl]-N-tert-butyl-piperazine-2-carboxamide;(alphaR,gammaS,2S)-N-[(1S)-2alpha-Hydroxyindan-1alpha-yl]-alpha-benzyl-gamma-hydroxy-2alpha-(tert-butylcarbamoyl)-1-piperazinepentanamide;(S)-1-[(2S,4R)-2-Hydroxy-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid tert-butylamide;[1(1S,2R),5(S)]-2,3,5-Trideoxy-N-(2,3-dihydro-2-hydroxy-1H-Inden-1-yl)-5-[2-[[(1,1-dimethyl)amino]carbonyl]-1-piperazinyl]-2-(phenylmethyl)-D-erythro-pentonamide;5-[2(S)-[(1,1-Dimethylethyl)aminocarbonyl]-1-piperazinyl]-4(S)-hydroxy-N-(2(R)-hydroxy-1(S)-indanyl)-2(R)-(phenylmethyl)pentanamide

Chemical Property of Desnicotinyl indinavir

Chemical Property:

• Vapor Pressure: 4.59E-28mmHg at 25°C
• Boiling Point: 814.7°C at 760 mmHg
• Flash Point: 446.5°C
• PSA: 123.16000
• Density: 1.22
• LogP: 3.17530
• Storage Temp.: Refrigerator
• Solubility.: Methanol
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 522.32060583
• Heavy Atom Count: 38
• Complexity: 781

Purity/Quality:

99% ^*data from raw suppliers

Des-3-pyridylmethylIndinavir(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)NC(=O)C1CNCCN1CC(CC(CC2=CC=CC=C2)C(=O)NC3C(CC4=CC=CC=C34)O)O
• Isomeric SMILES: CC(C)(C)NC(=O)[C@@H]1CNCCN1C[C@H](C[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H]3[C@@H](CC4=CC=CC=C34)O)O
• Uses: An Intermediate in the preparation of Indinavir and also a metabolite of Indinavir An Intermediate in the preparation of Indinavir and also a metabolite of Indinavir. It is a COVID19-related research product.

Technology Process of Desnicotinyl indinavir

There total 27 articles about Desnicotinyl indinavir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide (150323-37-8) → [14C]-N-Dealkyl Indinavir (150323-38-9)

Guidance literature:

With hydrogenchloride; In isopropyl alcohol; for 6h; Ambient temperature;

DOI:10.1021/jm00047a001

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → [14C]-N-Dealkyl Indinavir (150323-38-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h

3: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature

4: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

6: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

7: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C

8: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h / 0 - 20 °C

9: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; hydrogen fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

DOI:10.1021/jm00047a001

Reference yield:

(S)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (848482-93-9) → [14C]-N-Dealkyl Indinavir (150323-38-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 40percent NaOH / dioxane; H₂O / 14 h

2: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h

3: 96 percent / H₂ / 10percent Pd/C / methanol / 3 h

4: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

5: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

6: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C

7: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h / 0 - 20 °C

8: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; lithium hydroxide; sodium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm00047a001

upstream raw materials:

(S)-4-[(2S,4R)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-hydroxy-5-oxo-pentyl]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid tert-butyl ester

N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide

(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

MK 944a

L 754394

Refernces

• 1、 -. "RETROVIRAL PROTEASE INHIBITING PIPERAZINE COMPOUNDS". . . Retrieved 2008/06/13.
• 2、 Dorsey,Levin,McDaniel,Vacca,Guare,Darke,Zugay,Emini,Schleif,Quintero,Lin,Chen -,Holloway,Fitzgerald,Axel,Ostovic,Anderson,Huff. "L-735,524: The design of a potent and orally bioavailable HIV protease inhibitor". . p. 3443 - 3451. Retrieved 2007/10/02.