Dimethylformamide → HCID 22031098, compound

HRID 1792549Notes

Reaction equation

HRID 1792549 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:5][N:4]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.Cl[CH2:43][C:44]([NH2:46])=[O:45].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C(OCC)(=O)C>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[N:17]2[CH2:18][CH2:19][N:20]([CH2:43][C:44]([NH2:46])=[O:45])[CH2:21][CH2:22]2)=[CH:5][N:4]([C:23]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6580Chloroacetamide2×HCID 11430Potassium CarbonateHCID 22031305HCID 22031305, compound

Product 1

HCID 22031098HCID 22031098, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 54 mg 6-(3-methyl-1-trityl-1H-4-pyrazolyl)-4-piperazin-1-yl-quinoline obtained in Example 187, 9.4 mg 2-chloroacetamide, 16 mg potassium carbonate and 3 mL dimethylformamide was stirred at 115° C. for 5 hours. 3 mg of 2-chloroacetamide was added thereto, and the mixture was stirred at the same temperature for 3 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, then washed twice with water and then with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 41 mg of the title compound as a colorless amorphous.

Workup

  1. stirringthe mixture was stirred at the same temperature for 3 hours
  2. customthe organic layer was separated
  3. washwashed twice with water
  4. dry with materialwith brine and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7a8d08b950614f38a4875328e9f0b75e
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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