2-(Aminomethyl)-1,1,1-trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-pentanol → 1,1,1-Trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-2-({[1-(4-fluorophenyl)-6-methyl-1H-indazol-4-yl]amino}methyl)-4-methyl-2-pentanol

HRID 418809Notes

Reaction equation

HRID 418809 reaction equation
[NH2:1][CH2:2][C:3]([OH:21])([CH2:8][C:9]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])([CH3:11])[CH3:10])[C:4]([F:7])([F:6])[F:5].Br[C:23]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]2[C:24]=1[CH:25]=[N:26][N:27]2[C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1>>[F:5][C:4]([F:7])([F:6])[C:3]([CH2:2][NH:1][C:23]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]2[C:24]=1[CH:25]=[N:26][N:27]2[C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)([OH:21])[CH2:8][C:9]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 179365862-(Aminomethyl)-1,1,1-trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-pentanol2×HCID 576159341h-Indazole,4-bromo-1-(4-fluorophenyl)-6-methyl-2×

Product 1

HCID 119924331,1,1-Trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-2-({[1-(4-fluorophenyl)-6-methyl-1H-indazol-4-yl]amino}methyl)-4-methyl-2-pentanol

Procedure

Prepared similarly to Example 25 from 2-(aminomethyl)-1,1,1-trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-pentanol (Intermediate 18) and 4-bromo-1-(4-fluorophenyl)-6-methyl-1H-indazole (Intermediate 28). Purification was conducted by silica gel chromatography using the Flashmaster II (20 g cartridge) eluting with a 100:0 to 50:50 cyclohexane:ethyl acetate gradient over 40 minutes to give the title compound (26.7 mg)

Workup

  1. customPurification
  2. washeluting with a 100:0 to 50:50 cyclohexane

Sources & evidence

ORD record
ord-c236d47c11ff4a8099b92df91133b9a2
Source dataset
uspto-grants-2012_01
Patent number
US08093281B2

Reaction notes

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