Potassium Carbonate → HCID 86656533, compound

HRID 1970175Notes

Reaction equation

HRID 1970175 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[CH:47]([CH3:51])[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]([CH:47]([CH3:51])[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 1011182-BromopropanamideHCID 86656532HCID 86656532, compound

Product 1

HCID 86656533HCID 86656533, compoundYield 62.6%

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) (90 mg, 0.15 mmol) in DMF (2 mL) was added potassium carbonate (43 mg, 0.31 mmol) followed by 2-Bromo-propionamide (29 mg, 0.19 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 (60 mg, 60%).

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-ddf5614dadc1414b9ac5078971f1a8fa
Source dataset
uspto-grants-2013_04
Patent number
US08426604B2

Reaction notes

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