Water → HCID 23160307, compound

HRID 2246354Notes

Reaction equation

HRID 2246354 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=3)[N:11]=[CH:10][N:9]=2)=[N:3]1.[CH:19]1([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=2F)=[O:23])[CH2:21][CH2:20]1.C(O[K])(C)(C)C.O>CN(C)C(=O)C>[CH:19]1([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=2[O:18][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[N:11]=[CH:10][N:9]=[C:8]3[NH:7][C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)=[O:23])[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 23160368HCID 23160368, compoundHCID 231603824-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-olHCID 178418922HCID 178418922, compound

Product 1

HCID 23160307HCID 23160307, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

4-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol (70 mg; 0.290 mmol) and 63 mg (0.346 mmol) of cyclopropyl(2,3-difluorophenyl)methanone were added to a solution of 81 mg (0.723 mmol) of tert-butoxy potassium in 6 ml of N,N-dimethylacetamide and the mixture was stirred at 110° C. 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 silica gel chromatography (chloroform:methanol=10:1) to give 36 mg (yield: 31%) of the title compound as a colorless 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 silica gel chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-71e745767c4e489c9d706f3dd490aa2d
Source dataset
uspto-grants-2010_03
Patent number
US07687502B2

Reaction notes

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