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

HRID 886701Notes

Reaction equation

HRID 886701 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].[CH3:25][NH2:26]>O1CCCC1>[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:26][CH3:25])[C:21]([F:24])([F:22])[F:23])=[O:15]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 594874985-amino-1-(4-fluorophenyl)-N-{[2-(trifluoromethyl)-2-oxiranyl]methyl}-1H-pyrazole-4-carboxamide

Product 1

HCID 594874925-Amino-1-(4-fluorophenyl)-N-{3,3,3-trifluoro-2-hydroxy-2-[(methylamino)methyl]propyl}-1H-pyrazole-4-carboxamideYield 56.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of 5-amino-1-(4-fluorophenyl)-N-{[2-(trifluoromethyl)-2-oxiranyl]methyl}-1H-pyrazole-4-carboxamide (750 mg, 2.18 mmol) in anhydrous tetrahydrofuran (10 ml) was added methylamine (2M in tetrahydrofuran, 4 ml, 8 mmol) and stirred at 21° C. for 15 hours. It was evaporated to give a foam which was triturated with diethyl ether (ca. 5 ml). The resulting solid was filtered off and washed with a little diethyl ether and then petroleum ether)(40-60° to give the title compound (465 mg).

Workup

  1. customIt was evaporated
  2. customto give a foam which
  3. customwas triturated with diethyl ether (ca. 5 ml)
  4. filtrationThe resulting solid was filtered off
  5. washwashed with a little diethyl ether

Sources & evidence

ORD record
ord-f33b33194e8344fbae71ee0629102d5f
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

Loading…