Hydrazine → HCID 59355017, compound

HRID 2196425Notes

Reaction equation

HRID 2196425 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[C:35]1[N:39]([CH3:40])[N:38]=[CH:37][CH:36]=1)[C:5]([NH:7][C@@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]([F:31])([F:30])[F:29])[CH2:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)=[O:6].NN>CO.C1COCC1>[NH2:10][CH2:9][C@@H:8]([NH:7][C:5](=[O:6])[C:4]1[CH:32]=[CH:33][C:34]([C:35]2[N:39]([CH3:40])[N:38]=[CH:37][CH:36]=2)=[C:2]([Br:1])[CH:3]=1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]([F:31])([F:30])[F:29]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59354995HCID 59354995, compound

Product 1

HCID 59355017HCID 59355017, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-4-(1-methyl-1H-pyrazol-5-yl)benzamide (172 mg, 0.28 mmol) in MeOH/THF (4 mL, 1:1) at RT was added hydrazine (0.17 mL, 5.5 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 (60.4 mg, 45%).

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-30fe725837724326a556d11bb831d6a3
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

Loading…