1-Hydroxy-1-cyclopropanecarboxylic acid → N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-[4-(trifluoromethyl)phenyl]propan-2-yl]-1-hydroxy-cyclopropane-1-carboxamide

HRID 13173Notes

Reaction equation

HRID 13173 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)[C@@H:19]([NH2:21])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH:32][C:33]1([C:36](O)=[O:37])[CH2:35][CH2:34]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][CH:23]=4)[C@@H:19]([NH:21][C:36]([C:33]4([OH:32])[CH2:35][CH2:34]4)=[O:37])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27331601-Hydroxy-1-cyclopropanecarboxylic acidHCID 59339640(1R,2S)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-[4-(trifluoromethyl)phenyl]propan-2-amine

Product 1

HCID 59339802N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-[4-(trifluoromethyl)phenyl]propan-2-yl]-1-hydroxy-cyclopropane-1-carboxamide

Procedure

Prepared as described in Example 105 using (1R,2S)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-[4-(trifluoromethyl)phenyl]propan-2-amine (59a, 21 mg, 50 μmol) and 1-hydroxycyclopropanecarboxylic acid (14 mg, 150 μmol). Yield 10 mg (42%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0aeb66c12a724e109c4f1edd075567a2
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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