Potassium Carbonate → HCID 86654622, compound

HRID 2384840Notes

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

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

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

Sources & evidence

ORD record: ord-efc4451443b14ecfa3f677d2afeb0817
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263781B2

Reaction notes

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