CO2 EtOH CH3CN → 4-((4-Chlorobenzyl)oxy)-1-(2-((1R*,2S*)-2-(2-hydroxypropan-2-yl)cyclopropyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2202974Notes

Reaction equation

HRID 2202974 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[N:21]=[C:20]([CH:22]5[CH2:24][CH:23]5[C:25]([OH:28])([CH3:27])[CH3:26])[N:19]([CH3:29])[C:18]=4[CH:30]=3)[C:10](=[O:31])[CH:9]=2)=[CH:4][CH:3]=1.C(=O)=O.CCO.CC#N>>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[N:21]=[C:20]([C@@H:22]5[CH2:24][C@@H:23]5[C:25]([OH:28])([CH3:27])[CH3:26])[N:19]([CH3:29])[C:18]=4[CH:30]=3)[C:10](=[O:31])[CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 87190995CO2 EtOH CH3CNHCID 89691107HCID 89691107, compound

Product 1

HCID 1213862244-((4-Chlorobenzyl)oxy)-1-(2-((1R*,2S*)-2-(2-hydroxypropan-2-yl)cyclopropyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-oneYield 33.6%

Procedure

(1RS,2SR)-4-((4-Chlorobenzyl)oxy)-1-(2-(2-(2-hydroxypropan-2-yl)cyclopropyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (0.830 g) was resolved by a preparative SFC (CHIRALPAK AYH, CO2/EtOH/CH3CN=600/200/200) to give a white solid (351 mg, >99% ee). This solid was recrystallized from IPA to give the title compound (279 mg) as a white solid.

Workup

  1. customto give a white solid (351 mg, >99% ee)
  2. customThis solid was recrystallized from IPA

Sources & evidence

ORD record
ord-a6b482cdf6f749bfa4081bd7d053cb53
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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