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Ethylamine → 5-Amino-N-{2-[(ethylamino)methyl]-3,3,3-trifluoro-2-hydroxypropyl}-1-(4-fluorophenyl)-1H-pyrazole-4-carboxamide

HRID 886702
Notes
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Reaction equation

HRID 886702 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH:16][CH2:17][C:18]1([C:21]([F:24])([F:23])[F:22])[CH2:20][O:19]1)=[O:15].[CH2:25]([NH2:27])[CH3:26]>C(#N)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH:16][CH2:17][C:18]([CH2:20][NH:27][CH2:25][CH3:26])([OH:19])[C:21]([F:24])([F:22])[F:23])=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6341Ethylamine2×HCID 594874985-amino-1-(4-fluorophenyl)-N-{[2-(trifluoromethyl)-2-oxiranyl]methyl}-1H-pyrazole-4-carboxamide

Product 1

HCID 591872235-Amino-N-{2-[(ethylamino)methyl]-3,3,3-trifluoro-2-hydroxypropyl}-1-(4-fluorophenyl)-1H-pyrazole-4-carboxamideYield 101.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-amino-1-(4-fluorophenyl)-N-{[2-(trifluoromethyl)-2-oxiranyl]methyl}-1H-pyrazole-4-carb oxamide (2 g, 5.8 mmol) in acetonitrile (25 ml) was added ethylamine (5 ml, 23 mmol). The solution was stirred at room temperature for 24 hours under nitrogen before further ethylamine (2 ml) was added. The solution was concentrated under reduced pressure to give the title compound (2.290 g).

Workup

  1. additionwas added
  2. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-58d54b5951054a508189bed455f6d194
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08247377B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes