3-Hydrazinylpyridine hydrochloride → 3-(1,1-difluoroethyl)-1-(pyridin-3-yl)-1H-pyrazol-5-amine

HRID 631647Notes

Reaction equation

HRID 631647 reaction equation
Cl.[NH:2]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)[NH2:3].[F:10][C:11]([F:18])([CH3:17])[C:12](=O)[CH2:13][C:14]#[N:15]>>[F:10][C:11]([C:12]1[CH:13]=[C:14]([NH2:15])[N:2]([C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[N:3]=1)([F:18])[CH3:17]

Participants

3

Reactant 2

HCID 231434543-Hydrazinylpyridine hydrochlorideHCID 86653534HCID 86653534, compound

Product 1

HCID 668766943-(1,1-difluoroethyl)-1-(pyridin-3-yl)-1H-pyrazol-5-amineYield 9%

Procedure

3-Hydrazinopyridine hydrochloride (435 mg, 3.0 mmol) was treated with 4,4-difluoro-3-oxopentanenitrile (400 mg, 3.0 mmol) (prepared as described in Example 152A Step 1) according to the procedure in Example 161A Step 3 to afford 3-(1,1-difluoroethyl)-1-(pyridin-3-yl)-1H-pyrazol-5-amine (62 mg, 0.27 mmol, 9%). 1H NMR (300 MHz, MeOD) δ 8.86 (s, 1H), 8.60 (d, 1H), 8.12 (d, 1H), 7.62 (t, 1H), 5.82 (s, 1H), 1.92 (t, 3H); LC-MS (ESI) m/z 225 (M+H)+.

Sources & evidence

ORD record
ord-bf381fcdf72747c8b60c5aabecd057af
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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