Potassium Carbonate → HCID 69432389, compound

HRID 1269741Notes

Reaction equation

HRID 1269741 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][CH:9]=[CH:10][CH3:11].[NH:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][N:25]=[CH:24]3)=[O:20])[CH2:14][CH2:13]1>CN(C)C=O>[CH2:8]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][N:25]=[CH:24]3)=[O:20])[CH2:14][CH2:13]1)[CH:9]=[CH:10][CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11589Crotyl chlorideHCID 22933392HCID 22933392, compound

Product 1

HCID 69432389HCID 69432389, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (55.0 mg, 0.398 mmol) and 1-chloro-2-butene (17.8 mg, 0.197 mmol) were added to a solution of the N-(4-piperidinyl)-1H-indazole-5-carboxamide (40.0 mg, 0.164 mmol) obtained in Example 58 in N,N-dimethylformamide (1.2 ml), and the resulting mixture was stirred for 20 hours while being maintained at room temperature. The reaction solution was filtered and the filtrate was concentrated to dryness. The resulting crude product residue was purified by a silica gel column chromatography (eluent: chloroform/methanol/aqueous ammonia=20/1/0.1) to obtain N-[1-(but-2-enyl)piperidin-4-yl]-1H-indazole-5-carboxamide (26 mg, 54%).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe resulting crude product residue was purified by a silica gel column chromatography (eluent: chloroform/methanol/aqueous ammonia=20/1/0.1)

Sources & evidence

ORD record
ord-ad5745e99df04399b345b42d19bef010
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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