HCID 69017366, compound → HCID 57972105, compound

HRID 1799274Notes

Reaction equation

HRID 1799274 reaction equation
[F:1][C:2]1([F:35])[CH2:4][C@@H:3]1[CH2:5][O:6][C:7]1[CH:34]=[CH:33][C:10]([C:11]([NH:13][C@@H:14]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)[C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])=[O:12])=[CH:9][CH:8]=1.FC1(F)C[C@H]1COC1C=CC(C(N[C@@H](CC2C=CC(OC(F)(F)F)=CC=2)C(NCCO)=O)=O)=CC=1.OCCNC(=O)[C@H](NC(=O)C1C=CC=CC=1)CC1C=CC(OC(F)(F)F)=CC=1>>[F:1][C:2]1([F:35])[CH2:4][CH:3]1[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:13][C@@H:14]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][C:29]([F:30])([F:31])[F:32])=[CH:26][CH:27]=2)[C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])=[O:12])=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 69017366HCID 69017366, compoundHCID 69020422HCID 69020422, compoundHCID 86636529HCID 86636529, compound2×

Product 1

HCID 57972105HCID 57972105, compound

Procedure

4-[(2,2-Difluorocyclopropyl)methoxy]-N-{2-[(2-hydroxyethyl)amino]-2-oxo-1-[4-(trifluoromethoxy)benzyl]ethyl}benzamide prepared in Example 40 was separated into three stereoisomers A, B, and C by HPLC under conditions as in Example 10 to give the title compound (referred to as Isomer A). Isomer A was estimated to be a mixture of 4-{[(1R)-2,2-difluorocyclopropyl]methoxy}-N-{(1S)-2-[(2-hydroxyethyl)amino]-2-oxo-1-[4-(trifluoromethoxy)benzyl]ethyl}benzamide and 4-{[(1S)-2,2-difluorocyclopropyl]methoxy}-N-{(1S)-2-[(2-hydroxyethyl)amino]-2-oxo-1-[4-(trifluoromethoxy)benzyl]ethyl}benzamide. Isomer B and Isomer C were estimated to be 4-{[(1R or S)-2,2-difluorocyclopropyl]methoxy}-N-{(1R)-2-[(2-hydroxyethyl)amino]-2-oxo-1-[4-(trifluoromethoxy)benzyl]ethyl}benzamide and 4-{[(1S or R)-2,2-difluorocyclopropyl]methoxy}-N-{(1R)-2-[(2-hydroxyethyl)amino]-2-oxo-1-[4-(trifluoromethoxy)benzyl]ethyl}benzamide, respectively.

Workup

  1. custom4-[(2,2-Difluorocyclopropyl)methoxy]-N-{2-[(2-hydroxyethyl)amino]-2-oxo-1-[4-(trifluoromethoxy)benzyl]ethyl}benzamide prepared in Example 40 was separated into three stereoisomers A, B, and C by HPLC under conditions as in Example 10
  2. customto give the title compound (

Sources & evidence

ORD record
ord-7d1f53ded0fd4059a310557c7ac01d20
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

Loading…