Hydrazine → N-(2-amino-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

HRID 1961002Notes

Reaction equation

HRID 1961002 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C@@H:13]([NH:25][C:26]([C:28]1[S:29][C:30]([C:33]2[N:37]([CH3:38])[N:36]=[CH:35][CH:34]=2)=[CH:31][CH:32]=1)=[O:27])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([F:24])([F:23])[F:22].NN>CO.C1COCC1>[NH2:3][CH2:12][CH:13]([NH:25][C:26]([C:28]1[S:29][C:30]([C:33]2[N:37]([CH3:38])[N:36]=[CH:35][CH:34]=2)=[CH:31][CH:32]=1)=[O:27])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([F:24])([F:23])[F:22]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57826603N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

Product 1

HCID 67066052N-(2-amino-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide (74 mg, 0.14 mmol) in MeOH/THF (2 mL, 1:1) at RT was added hydrazine (86 μL, 2.75 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.

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-b4225d321d7a4243857753bb1dc93655
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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