Hydrazine → N-((1S)-2-amino-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-fluoro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)benzamide

HRID 2196419Notes

Reaction equation

HRID 2196419 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:41])[C:6]=1[C:7]1[CH:39]=[CH:38][C:10]([C:11]([NH:13][C@@H:14]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:36])[F:35])[CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)=[O:12])=[CH:9][C:8]=1[F:40].NN>CO.C1COCC1>[NH2:16][CH2:15][C@@H:14]([NH:13][C:11](=[O:12])[C:10]1[CH:38]=[CH:39][C:7]([C:6]2[N:5]([CH3:41])[N:4]=[CH:3][C:2]=2[Cl:1])=[C:8]([F:40])[CH:9]=1)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([F:37])([F:36])[F:35]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 593550284-(4-chloro-1-methyl-1H-pyrazol-5-yl)-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-fluorobenzamide

Product 1

HCID 59355023N-((1S)-2-amino-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-fluoro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)benzamideYield 21%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-fluorobenzamide (90 mg, 0.15 mmol) in MeOH/THF (2 mL, 1:1) at RT was added hydrazine (0.12 mL, 3.93 mmol). After stirring for 18 h at RT, the reaction solution was concentrated under vacuum and purified via column chromatography (silica, 3% MeOH in DCM (1% NH4OH)) yielding the title compound (14 mg, 21%).

Workup

  1. concentrationthe reaction solution was concentrated under vacuum
  2. custompurified via column chromatography (silica, 3% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-f70016fd568748d39d2a5c506ab64a02
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

Loading…