Potassium Carbonate → HCID 86654581, compound

HRID 1949462Notes

Reaction equation

HRID 1949462 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-5609d2ccbb44499f969f7107cc3f341f
Source dataset
uspto-grants-2013_03
Patent number
US08399681B2

Reaction notes

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