Potassium Carbonate → HCID 76021232, compound

HRID 1970174Notes

Reaction equation

HRID 1970174 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=[C:16]3[S:20][C:19]([N:21]([CH3:28])[CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[N:18][C:17]3=[O:29])=[CH:12][CH:13]=2)[CH:8]=[N:7]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:47][C:48]([NH2:50])=[O:49]>CN(C=O)C>[F:39][C:2]([F:38])([F:1])[C:3]1[CH:33]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=[C:16]3[S:20][C:19]([N:21]([CH3:28])[CH:22]4[CH2:23][CH2:24][N:25]([CH2:47][C:48]([NH2:50])=[O:49])[CH2:26][CH2:27]4)=[N:18][C:17]3=[O:29])=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 86656532HCID 86656532, compound

Product 1

HCID 76021232HCID 76021232, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[1-(2,4-Bis-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-(methyl-piperidin-4-yl-amino)-thiazol-4-one (Example 17) (80 mg, 0.14 mmol) in DMF (2 mL) was added potassium carbonate (39 mg, 0.28 mmol) followed by 2-Bromo-acetamide (23 mg, 0.17 mmol). The reaction mixture was stirred at room temperature for 4 hours and partitioned between water and ethyl acetate. The ethyl acetate layer was washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid. The crude solid was purified via flash chromatography (5% methanol in dichloromethane) to yield the title compound (61 mg, 69%).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude solid
  7. customThe crude solid was purified via flash chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5db414ca33954a55996f81bdde5762ae
Source dataset
uspto-grants-2013_04
Patent number
US08426604B2

Reaction notes

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