Water → HCID 11662739, compound

HRID 2246319Notes

Reaction equation

HRID 2246319 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[S:14][C:15]2[C:20]([N:21]=1)=[CH:19][CH:18]=[CH:17][N:16]=2.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH3:32])(=[O:31])=[O:30])[C:24]=1F.[K].O>CN(C)C(=O)C>[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH3:32])(=[O:31])=[O:30])[C:24]=1[O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[S:14][C:15]2[C:20]([N:21]=1)=[CH:19][CH:18]=[CH:17][N:16]=2

Participants

6

Reactant 4

HCID 962WaterHCID 5462222PotassiumHCID 11666499HCID 11666499, compoundHCID 22747447HCID 22747447, compound

Product 1

HCID 11662739HCID 11662739, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(6-Hydroxy-quinazolin-4-yl)-thiazolo[5,4-b]pyridin-2-yl-amine (100 mg; 0.34 mmol) and 116 mg (0.61 mmol) of 1,2-difluoro-3-methanesulfonylbenzene were added to a solution of 120 mg (0.61 mmol) of tert-buxoty potassium in 5 ml of N,N-dimethylacetamide and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution and the mixture was extracted with chloroform. The organic layer was dried and concentrated and the resulting residue was purified by a thin layer silica gel chromatography (chloroform:methanol=10:1) to give 81 mg (yield: 51%) of the title compound as a yellow solid.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe resulting residue was purified by a thin layer silica gel chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-4967c750957e4bee945c23ed7ce88c9f
Source dataset
uspto-grants-2010_03
Patent number
US07687502B2

Reaction notes

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