Formic Acid → N,N-dipropyl-5-(trifluoromethyl)-1H-pyrazol-3-amine

HRID 528958Notes

Reaction equation

C([N:8]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[N:9]1)C1C=CC=CC=1.C(O)=O>CCO.[Pd]>[CH2:21]([N:17]([CH2:18][CH2:19][CH3:20])[C:10]1[CH:11]=[C:12]([C:13]([F:15])([F:16])[F:14])[NH:8][N:9]=1)[CH2:22][CH3:23]

Participants

Conditions

Temperature: 78 °C

Procedure

To a 1 dram pressure vial containing 1-benzyl-N,N-dipropyl-5-(trifluoromethyl)-1H-pyrazol-3-amine (597 mg, 1.83 mmol) in EtOH (9.2 mL) was added 10% Pd/C (585 mg, 5.50 mmol) followed by dropwise addition of formic acid (3.9 mL, 101.0 mmol). The vial was capped, and the resulting black reaction mixture was heated at 78° C. for 1 h. The reaction mixture was filtered through a pad of CELITE® and concentrated in vacuo to give the title compound (401 mg, 93%) as a white solid. 1H NMR (CDCl3) δ 5.58 (s, 1H), 3.18-3.11 (m, 4H), 1.69-1.50 (m, 4H), 0.94 (t, J=7.4 Hz, 6H); MS(ESI+) m/z 236.2 (M+H)+.

Workup

customThe vial was capped
filtrationThe reaction mixture was filtered through a pad of CELITE®
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-19f4d4c28acb4b57920e5e32d2403dc7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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