Dimethylformamide → HCID 67783220, compound

HRID 1647824Notes

Reaction equation

HRID 1647824 reaction equation
[CH:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH:4]=[C:3]([C:14]([C@:16]2([CH3:36])[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([O:26][CH3:27])[C:23]=4[NH2:25])[N:18]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:17]2=[O:35])=[O:15])[N:2]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.CI.[C:39](=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.O>[CH3:39][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]2[CH:4]=[C:3]([C:14]([C@:16]3([CH3:36])[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([O:26][CH3:27])[C:23]=4[NH2:25])[N:18]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[C:17]3=[O:35])=[O:15])[N:2]=[CH:1][C:6]1=2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67783620HCID 67783620, compound

Product 1

HCID 67783220HCID 67783220, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.55 g of (S)-3-{9H-pyrido[3,4-b]-indol-3-yl-carbonyl}-amino-3-methyl-1-(4-fluorophenyl)-5-methoxy-2-indolinone, 0.2 ml of methyl iodide, 0.78 g of potassium carbonate and 10 ml of dimethylformamide was stirred at room temperature for 3 hours, and water and ethyl acetate were added to the mixture. The organic layer was separated, washed, dried, and evaporated under reduced pressure. The residue was crystallized from a mixed solvent of hexane and ethyl acetate to afford 0.403 g of the title compound as pale yellow crystals. Melting point: 232° to 233° C., [α]D20 : 0° (c=0.214, CHCl3)

Workup

  1. customThe organic layer was separated
  2. washwashed
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was crystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-05fdac4b38d74112bea2573f4cb71eaa
Source dataset
uspto-grants-1995_07
Patent number
US05434148

Reaction notes

Loading…