Potassium Carbonate → HCID 86654581, compound

HRID 2384719Notes

Reaction equation

HRID 2384719 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[C:17]4[S:21][C:20]([N:22]5[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[N:19][C:18]4=[O:29])=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:32]([F:35])([F:34])[F:33])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:42][C:43]([F:51])([F:50])[CH2:44]OS(C)(=O)=O>CS(C)=O>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[C:17]4[S:21][C:20]([N:22]5[CH2:28][CH2:27][CH2:26][N:25]([CH2:44][C:43]([F:51])([F:50])[F:42])[CH2:24][CH2:23]5)=[N:19][C:18]4=[O:29])=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:32]([F:35])([F:34])[F:33])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5565652,2,2-Trifluoroethyl MethanesulfonateHCID 67240905HCID 67240905, compound

Product 1

HCID 86654581HCID 86654581, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 5-[1-(4-Chloro-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-[1,4]diazepan-1-yl-thiazol-4-one (0.051 g, 0.098 mmol) in DMSO (2.2 mL) was treated with potassium carbonate (0.045 g, 0.32 mmol) and methanesulfonic acid 2,2,2-trifluoro-ethyl ester (0.06 g, 0.32 mmol). Reaction mixture was stirred at 70° C. for 1 hour and partitioned between dichloromethane and water. The dichloromethane layer was dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid. The crude solid was purified using semi-preparative reverse phase HPLC (YMC ODS A, 100×30 mm, 50 μM I.D., 0.05% TFA acetonitrile/0.05% TFA water=30/70 to 100/0) to yield the title compound as a flocculent solid.

Workup

  1. customReaction mixture
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe dichloromethane layer was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude solid
  7. customThe crude solid was purified

Sources & evidence

ORD record
ord-8788f7994ff34392ab611741c2a2d61b
Source dataset
uspto-grants-2012_09
Patent number
US08263781B2

Reaction notes

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