Hydrochloric Acid → HCID 67499057, compound

HRID 1484738Notes

Reaction equation

HRID 1484738 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]([CH:19]=[O:20])=[N:9]2)[CH:5]=[N:6][CH:7]=1.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[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][OH:20])=[N:9]2)[CH:5]=[N:6][CH:7]=1.[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:18])[CH:15]([CH3:16])[CH3:17])[CH:10]=[N:9]2)[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86664683HCID 86664683, compound

Product 2

HCID 67499057HCID 67499057, compoundYield 56.7%HCID 67499813HCID 67499813, compoundYield 3.18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(1-(5-fluoropyridin-3-yl)-3-formyl-1H-pyrazol-4-yl)isobutyramide (0.315 g, 1.140 mmol) in methanol (5.70 ml) at 0° C. was added sodium borohydride (0.086 g, 2.280 mmol). The reaction was stirred at 0° C. for 2 hours, and room temperature for 20 hours. 0.5 M HCl was added, the reaction was neutralized with saturated aqueous sodium bicarbonate, and the mixture was extracted with dichloromethane. The organic phases were concentrated and chromatographed (0-100% ethyl acetate/hexanes) to give N-(1-(5-fluoropyridin-3-yl)-3-(hydroxymethyl)-1H-pyrazol-4-yl)isobutyramide (180 mg, 0.647 mmol, 56.7%) as a white solid and N-(1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-yl)isobutyramide (9 mg, 0.036 mmol, 3.18%) as a white solid.

Workup

  1. waitroom temperature for 20 hours
  2. extractionthe mixture was extracted with dichloromethane
  3. concentrationThe organic phases were concentrated
  4. customchromatographed (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bb2bd2933978473cb0890c29f55052e0
Source dataset
uspto-grants-2016_08
Patent number
US09422278B2

Reaction notes

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