(1S,2S,4R)-4-[4-[[(1S)-2,3-Dihydro-1H-inden-1-yl]aMino]-7H-pyrrolo[2,3-d]pyriMidin-7-yl]-2-hydroxy-cyclopentaneMethanol

Base Information

• Chemical Name: (1S,2S,4R)-4-[4-[[(1S)-2,3-Dihydro-1H-inden-1-yl]aMino]-7H-pyrrolo[2,3-d]pyriMidin-7-yl]-2-hydroxy-cyclopentaneMethanol
• CAS No.: 905580-90-7
• Molecular Formula: C21H24N4O2
• Molecular Weight: 364.447
• Mol file: 905580-90-7.mol

Synonyms:(1S,2S,4R)-4-[4-[[(1S)-2,3-Dihydro-1H-inden-1-yl]aMino]-7H-pyrrolo[2,3-d]pyriMidin-7-yl]-2-hydroxy-cyclopentaneMethanol;DesulfonaMide MLN 4924;(1S,2S,4R)-4-(4-((S)-2,3-dihydro-1H-inden-1-ylaMino)-7H-pyrrolo[2,3-d]pyriMidin-7-yl)-2-(hydroxyMethyl)cyclopentanol

Chemical Property of (1S,2S,4R)-4-[4-[[(1S)-2,3-Dihydro-1H-inden-1-yl]aMino]-7H-pyrrolo[2,3-d]pyriMidin-7-yl]-2-hydroxy-cyclopentaneMethanol

Chemical Property:

• Boiling Point: 637.3±55.0 °C(Predicted)
• PKA: 14.16±0.60(Predicted)
• PSA: 83.20000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 2.90800
• Solubility.: Methanol, Tetrahydrofuran

Purity/Quality:

97% ^*data from raw suppliers

Desulfonamide MLN 4924 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of MLN 4924 (M425100).

Technology Process of (1S,2S,4R)-4-[4-[[(1S)-2,3-Dihydro-1H-inden-1-yl]aMino]-7H-pyrrolo[2,3-d]pyriMidin-7-yl]-2-hydroxy-cyclopentaneMethanol

There total 21 articles about (1S,2S,4R)-4-[4-[[(1S)-2,3-Dihydro-1H-inden-1-yl]aMino]-7H-pyrrolo[2,3-d]pyriMidin-7-yl]-2-hydroxy-cyclopentaneMethanol 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: 98.0%

N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-7-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (905580-89-4) → (1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(hydroxymethyl)-cyclopentanol (905580-90-7)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 20 ℃; for 60h;

Reference yield: 81.1%

(1S,2S,4R)-4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxylmethyl)cyclopentanol (1113025-27-6) + (S)-2,3-dihydro-1H-inden-1-amine hydrochloride (32457-23-1,10305-73-4) → (1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(hydroxymethyl)-cyclopentanol (905580-90-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In iso-butanol; at 130 ℃; under 4500.45 Torr; Large scale;

DOI:10.1021/acs.oprd.5b00209

Reference yield:

(1S,2S,4R)-4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxylmethyl)cyclopentanol (1113025-27-6) + (S)-1-Aminoindane (10277-74-4,34698-41-4,61341-86-4,61949-83-5) → (1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(hydroxymethyl)-cyclopentanol (905580-90-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In iso-butanol; at 55 - 135 ℃; under 6000.6 Torr;

upstream raw materials:

N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-7-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

(1S,2S,4R)-4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxylmethyl)cyclopentanol

(S)-1-Aminoindane

[(1S,3S,5S)-3-(tritylamino)-6-oxabicyclo[3.1.0]hex-1-yl]methanol

Downstream raw materials:

((1S,2S,4R)-4-(4-(((S)-2,3-dihydro-1H-inden-1-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxycyclopentyl)-methyl sulfamate

((1S,2S,4R)-4-(4-(((S)-2,3-dihydro-1H-inden-1-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxycyclopentyl)-methyl sulfamate hydrochloride

Refernces

• 1、 Armitage, Ian,Elliott, Eric L.,Hicks, Frederick,Langston, Marianne,McCarron, Ashley,McCubbin, Quentin J.,Obrien, Erin,Stirling, Matt,Zhu, Lei. "Process Development and GMP Production of a Potent NAE Inhibitor Pevonedistat". . p. 1299 - 1307. Retrieved 2015/09/28.
• 2、 -. "Inhibitors of E1 activating enzymes". Page/Page column 52. . Retrieved 2010/11/28.