Potassium Carbonate → HCID 86654622, compound

HRID 1949588Notes

Reaction equation

HRID 1949588 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[S:9][C:10](=[CH:14][C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=3[C:35]([F:38])([F:37])[F:36])[N:19]=[CH:18]4)[C:11](=[O:13])[N:12]=2)[CH2:3]1.[F:39][CH:40]([F:50])[CH2:41]OS(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:36][C:35]([F:38])([F:37])[C:26]1[CH:27]=[C:28]([C:31]([F:34])([F:32])[F:33])[CH:29]=[CH:30][C:25]=1[CH2:24][N:20]1[C:21]2[C:17](=[CH:16][C:15]([CH:14]=[C:10]3[S:9][C:8]([N:4]4[CH2:5][CH2:6][CH2:7][C@H:2]([NH:1][CH2:41][CH:40]([F:50])[F:39])[CH2:3]4)=[N:12][C:11]3=[O:13])=[CH:23][CH:22]=2)[CH:18]=[N:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 86654563HCID 86654563, compound

Product 1

HCID 86654622HCID 86654622, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of DMF (1 mL) was added 2-(3-(S)-Amino-piperidin-1-yl)-5-[1-(2,4-bis-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-thiazol-4-one (0.03 g, 0.05 mmol), Trifluoro-methanesulfonic acid 2,2-difluoro-ethyl ester (0.02 g, 0.09 mmol) and potassium carbonate (0.014 g, 0.1 mmol). The resulting mixture was heated at 70° C. overnight and partitioned between dichloromethane and water. The combined organic extracts were washed with brine, dried, and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with MeOH/CH2Cl2 (7/93) to afford the title product.

Workup

  1. custompartitioned between dichloromethane and water
  2. washThe combined organic extracts were washed with brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with MeOH/CH2Cl2 (7/93)

Sources & evidence

ORD record
ord-09546bfd8ac7470ea003959a603d0414
Source dataset
uspto-grants-2013_03
Patent number
US08399681B2

Reaction notes

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