N-[(1R)-2-[[(1S,2R,3S)-1-(Cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]amino]-2-oxo-1-(thiazol-4-ylmethyl)ethyl]-1H-benzo[D]imidazole-2-carboxamide

Base Information

• Chemical Name: N-[(1R)-2-[[(1S,2R,3S)-1-(Cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]amino]-2-oxo-1-(thiazol-4-ylmethyl)ethyl]-1H-benzo[D]imidazole-2-carboxamide
• CAS No.: 134362-79-1
• Molecular Formula: C₂₇H₃₅N₅O₄S
• Molecular Weight: 525.672
• ChEMBL ID: CHEMBL190141
• DSSTox Substance ID: DTXSID20470221
• Pharos Ligand ID: 6A1N82TS9B4T
• Wikidata: Q82298228
• Mol file: 134362-79-1.mol

Synonyms:Ro 0437626;134362-79-1;CHEMBL190141;N-[(1R)-2-[[(1S,2R,3S)-1-(CYCLOHEXYLMETHYL)-3-CYCLOPROPYL-2,3-DIHYDROXYPROPYL]AMINO]-2-OXO-1-(THIAZOL-4-YLMETHYL)ETHYL]-1H-BENZO[D]IMIDAZOLE-2-CARBOXAMIDE;RO-0437626;1H-Benzoimidazole-2-carboxylic acid[(R)-1-((1S,2R,3S)-1-cyclo-hexylmethyl-3-cyclopropyl-2,3-dihydroxy-propylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide;N-[(1R)-2-[[(1S,2R,3S)-1-(Cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]amino]-2-oxo-1-(4-thiazolylmethyl)ethyl]-1H-benzimidazole-2-carboxamide;N-[(2R)-1-[[(2S,3R,4S)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]amino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]-1H-benzimidazole-2-carboxamide;SCHEMBL16507547;DTXSID20470221;Ro 116-6446/008;BDBM50168286;AKOS024456978;NCGC00378583-01;HY-108673;CS-0029443;J-006525;1H-Benzoimidazole-2-carboxylic acid [(R)-1-((1S,2R,3S)-1-cyclohexylmethyl-3-cyclopropyl-2,3-dihydroxy-propylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide;N-[(1R)-2-[[(1S,2R,3S)-1-(Cyclohexy lmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]amino]- 2-oxo-1-(4-thiazolylmethyl)ethyl]-1H-benzimidazole -2-carboxamide

Chemical Property of N-[(1R)-2-[[(1S,2R,3S)-1-(Cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]amino]-2-oxo-1-(thiazol-4-ylmethyl)ethyl]-1H-benzo[D]imidazole-2-carboxamide

Chemical Property:

• PSA: 168.47000
• LogP: 3.72930
• Storage Temp.: Store at -20°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 525.24097579
• Heavy Atom Count: 37
• Complexity: 780

Purity/Quality:

≥98% by HPLC ^*data from raw suppliers

Ro 0437626 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)CC(C(C(C2CC2)O)O)NC(=O)C(CC3=CSC=N3)NC(=O)C4=NC5=CC=CC=C5N4
• Isomeric SMILES: C1CCC(CC1)C[C@@H]([C@H]([C@H](C2CC2)O)O)NC(=O)[C@@H](CC3=CSC=N3)NC(=O)C4=NC5=CC=CC=C5N4
• Uses: Ro 0437626 is a P2X1 purinergic receptor antagonist.

Technology Process of N-[(1R)-2-[[(1S,2R,3S)-1-(Cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]amino]-2-oxo-1-(thiazol-4-ylmethyl)ethyl]-1H-benzo[D]imidazole-2-carboxamide

There total 6 articles about N-[(1R)-2-[[(1S,2R,3S)-1-(Cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]amino]-2-oxo-1-(thiazol-4-ylmethyl)ethyl]-1H-benzo[D]imidazole-2-carboxamide 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: 51.0%

2-(R)-amino-N-[(1-(S)-cyclohexylmethyl-3-cyclopropyl-2-(R),3-(S)-dihydroxypropyl)amino]-3-thiazol-4-yl-propionamide (134362-77-9) + 2-benzimidazolecarboxylic acid (2849-93-6) → Ro 0437626 (134362-79-1)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 8h;

DOI:10.1016/j.bmcl.2005.04.049

Reference yield:

(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-butane-1,2-diol (134362-04-2) → Ro 0437626 (134362-79-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / triethylamine; PyBOP / dimethylformamide / 8 h / 20 °C

2: 98 percent / TFA / CH₂Cl₂ / 4 h / 20 °C

3: 51 percent / triethylamine; PyBOP / dimethylformamide / 8 h / 20 °C

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.04.049

Reference yield:

(1-(S)-cyclohexylmethyl-3-cyclopropyl-2-(R)-hydroxy-3-oxo-propyl)carbamic acid ethyl ester (861807-51-4) → Ro 0437626 (134362-79-1)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium triacetoxyborohydride / heptane; acetonitrile / 4 h / 20 - 24 °C

2: 1.09 g / aq. KOH / methanol / 18 h / Heating

3: 77 percent / triethylamine; PyBOP / dimethylformamide / 8 h / 20 °C

4: 98 percent / TFA / CH₂Cl₂ / 4 h / 20 °C

5: 51 percent / triethylamine; PyBOP / dimethylformamide / 8 h / 20 °C

With potassium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium tris(acetoxy)borohydride; triethylamine; trifluoroacetic acid; In methanol; n-heptane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmcl.2005.04.049

upstream raw materials:

2-(R)-amino-N-[(1-(S)-cyclohexylmethyl-3-cyclopropyl-2-(R),3-(S)-dihydroxypropyl)amino]-3-thiazol-4-yl-propionamide

2-benzimidazolecarboxylic acid

(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-butane-1,2-diol

(1-(S)-cyclohexylmethyl-3-cyclopropyl-2-(R)-hydroxy-3-oxo-propyl)carbamic acid ethyl ester

Refernces