Thionyl Chloride → HCID 67499807, compound

HRID 1484739Notes

Reaction equation

HRID 1484739 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[C:10]([CH2:19]O)=[N:9]2)[CH:5]=[N:6][CH:7]=1.S(Cl)([Cl:23])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:23][CH2:19][C:10]1[C:11]([NH:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])=[CH:12][N:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=2)[N:9]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 67499057HCID 67499057, compound

Product 1

HCID 67499807HCID 67499807, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-(5-fluoropyridin-3-yl)-3-(hydroxymethyl)-1H-pyrazol-4-yl)isobutyramide (0.100 g, 0.359 mmol) in dichloromethane (3.59 ml) was added thionyl chloride (0.157 ml, 2.151 mmol). The reaction was stirred at room temperature for 2 hours. Saturated aqueous sodium bicarbonate was added, and the mixture was extracted with dichloromethane. The combined organic phases were washed with brine and concentrated to give N-(3-(chloromethyl)-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-yl)isobutyramide (100 mg, 0.337 mmol, 94% yield) as a white solid: mp 172.0-177.0° C.; 1H NMR (400 MHz, CDCl3) δ 8.79 (s, 1H), 8.67 (s, 1H), 8.40 (s, 1H), 7.80 (dt, J=9.4, 2.3 Hz, 1H), 7.42 (s, 1H), 4.77 (s, 2H), 2.63 (hept, J=6.9 Hz, 1H), 1.30 (d, J=6.9 Hz, 6H); ESIMS m/z 298 ([M+H]+).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe combined organic phases were washed with brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-135d8b4309e24b47b7ad67f7af809dfc
Source dataset
uspto-grants-2016_08
Patent number
US09422278B2

Reaction notes

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