Potassium Carbonate → HCID 86703392, compound

HRID 512561Notes

Reaction equation

HRID 512561 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:32])[NH:12][C:13]2[S:17][C:16]([NH:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)=[N:15][C:14]=2[C:29](=[O:31])[NH2:30])=[CH:7][CH:6]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:12][C:13]2[S:17][C:16]([NH:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)=[N:15][C:14]=2[C:29]([NH2:30])=[O:31])=[O:32])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86703393HCID 86703393, compound

Product 1

HCID 86703392HCID 86703392, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-{[4-carbamoyl-2-(naphthalen-2-ylamino)thiazol-5-yl]carbamoyl}phenyl acetate (100 mg, 0.22 mmol) in MeOH (10 mL) was added K2CO3 (93 mg, 0.67 mmol) at rt, and the mixture was stirred for 1 h. The reaction mixture was concentrated, and the residue was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting solids were collected by filtration and washed with MeOH to give 60 mg (68% yield) of the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. filtrationThe resulting solids were collected by filtration
  7. washwashed with MeOH

Sources & evidence

ORD record
ord-e6ddeab823354ec99480a2c299157688
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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