Benzylamine → 5-Amino-1-(4-fluorophenyl)-N-(3,3,3-trifluoro-2-hydroxy-2-{[(phenylmethyl)amino]methyl}propyl)-1H-pyrazole-4-carboxamide

HRID 886717Notes

Reaction equation

HRID 886717 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]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCOCC1>[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]([OH:19])([CH2:20][NH:32][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:21]([F:22])([F:23])[F:24])=[O:15]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 594874985-amino-1-(4-fluorophenyl)-N-{[2-(trifluoromethyl)-2-oxiranyl]methyl}-1H-pyrazole-4-carboxamide

Product 1

HCID 594874975-Amino-1-(4-fluorophenyl)-N-(3,3,3-trifluoro-2-hydroxy-2-{[(phenylmethyl)amino]methyl}propyl)-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 5-amino-1-(4-fluorophenyl)-N-{[2-(trifluoromethyl)-2-oxiranyl]methyl}-1H-pyrazole-4-carboxamide (15.3 g) in dioxane (250 ml) was added benzylamine (5.76 ml). The mixture was stirred at room temperature for 16 hours and then for a further 4 hours to ensure the reaction was complete. The orange solution was concentrated in vacuo to give an orange oil (which still contained some solvent). The oil was dried on the vacuum line to give the title compound (20.50 g) as an orange solid.

Workup

  1. waitfor a further 4 hours to ensure
  2. concentrationThe orange solution was concentrated in vacuo
  3. customto give an orange oil (which
  4. customThe oil was dried on the vacuum line

Sources & evidence

ORD record
ord-8e0426ccceb94ef191e43546e34cdb70
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

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