Water → HCID 23160358, compound

HRID 2246315Notes

Reaction equation

HRID 2246315 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.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[C:21]=1F.C(O[K])(C)(C)C.O>CN(C)C(=O)C>[F:19][C:20]1[CH:21]=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:23]=[CH:24][C:25]=1[O:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[NH:7][C:4]1[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 22747447HCID 22747447, compoundHCID 231603824-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-olHCID 178418922HCID 178418922, compound

Product 1

HCID 23160358HCID 23160358, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
77 °C

Procedure

4-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol (250 mg; 1.033 mmol) and 424 mg (2.219 mmol) of the above-prepared sulfone compound were added to a solution of 320 mg (2.857 mmol) of tert-butoxy potassium in 24 ml of N,N-dimethylacetamide and the mixture was stirred at 77° C. for 12 hours. To the reaction solution was added water followed by extracting with chloroform. The organic layer was dried and concentrated and the resulting residue was purified by a reversed phase preparative HPLC (0.1% TFA-containing water:acetonitrile=90:10→10:90) to give 120 mg (yield: 28%) of the title compound as a yellow solid.

Workup

  1. extractionby extracting with chloroform
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe resulting residue was purified by a reversed phase preparative HPLC (0.1% TFA-containing water:acetonitrile=90:10→10:90)

Sources & evidence

ORD record
ord-ce014e2564ba4187bd00af1d48be365b
Source dataset
uspto-grants-2010_03
Patent number
US07687502B2

Reaction notes

Loading…