Dimethylformamide → HCID 66794993, compound

HRID 1057195Notes

Reaction equation

HRID 1057195 reaction equation
IC.[CH:3]1(/[C:7](/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:8](/[C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=2)\[C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[CH:12]3)[CH2:6][CH2:5][CH2:4]1.[C:37]([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[CH:3]1(/[C:7](/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:8](/[C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=2)\[C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:37])[N:13]=[CH:12]3)[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86675645HCID 86675645, compound

Product 1

HCID 66794993HCID 66794993, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodomethane (80 mg, 0.84 mmol) was added to a mixture of (E)-ethyl 3-(4-((E)-2-cyclobutyl-1-(1H-indazol-5-yl)-2-phenylvinyl)phenyl)acrylate (0.25 g, 0.56 mmol; intermediate in the preparation of Compound 155), K2CO3 (0.12 g, 0.84 mmol), and DMF (5.6 mL) at room temperature. The resulting mixture was stirred overnight, diluted with water, and extracted with EtOAc. The extract was washed with water, washed with brine, dried over sodium sulfate, filtered, concentrated, and then purified on a silica gel column using 0-50% EtOAc in hexanes to afford the title compound. LCMS: 463 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with water
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on a silica gel column

Sources & evidence

ORD record
ord-58242053dacc4c48939adbdc5abc561c
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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