Potassium Carbonate → HCID 86656535, compound

HRID 1970179Notes

Reaction equation

HRID 1970179 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][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]([CH3:27])[CH:22]4[CH2:26][CH2:25][NH:24][CH2:23]4)=[N:18][C:17]3=[O:28])=[CH:12][CH:13]=2)[CH:8]=[N:7]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:46][C:47]([NH2:49])=[O:48]>CN(C=O)C>[F:38][C:2]([F:37])([F:1])[C:3]1[CH:32]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:30]=[CH:29][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]([CH3:27])[C@@H:22]4[CH2:26][CH2:25][N:24]([CH2:46][C:47]([NH2:49])=[O:48])[CH2:23]4)=[N:18][C:17]3=[O:28])=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 86656536HCID 86656536, compound

Product 1

HCID 86656535HCID 86656535, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[1-(2,4-Bis-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-(methyl-pyrrolidin-3-yl-amino)-thiazol-4-one (100 mg, 0.18 mmol) in DMF (2 mL) was added potassium carbonate (74 mg, 0.54 mmol) followed by 2-Bromo-acetamide (30 mg, 0.21 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 (82 mg, 75%).

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-56f5e6f21e0b4d8e81ff5f7b155151e9
Source dataset
uspto-grants-2013_04
Patent number
US08426604B2

Reaction notes

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