Ammonia → HCID 58656497, compound

HRID 1988935Notes

Reaction equation

HRID 1988935 reaction equation
[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:26][C:27]([O:29][CH3:30])=[O:28].N>CN(C=O)C>[CH:1]1([NH:4][C:5]([C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[N:17]=[CH:16]4)[CH:7]=2)=[O:22])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 7295Methyl chloroacetateHCID 24758Sodium hydrideHCID 10469531N-cyclopropyl-3-(1H-indazol-5-yl)-4-methylbenzamide

Product 1

HCID 58656497HCID 58656497, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-cyclopropyl-3-(1H-indazol-5-yl)-4-methylbenzamide (Example 17) (0.65 g) in dry DMF (26 ml) was treated with sodium hydride (60% oil dispersion, 0.134 g) under nitrogen. After 5 min methyl chloroacetate (0.29 g) was added and the mixture was stirred for 2 h. Aqueous ammonia (2M, 10 ml) was added and the solvent was removed under vacuum. The residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (2:1 to 1:1) to give the title compound (0.56 g).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (2:1 to 1:1)

Sources & evidence

ORD record
ord-c03e69e8fde64fb99923526affcd8867
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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