Water → HCID 67298585, compound

HRID 1520333Notes

Reaction equation

HRID 1520333 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[N:6]=[C:5]2[NH:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH2:23])=[O:22].Br[CH2:29][CH2:30][Cl:31].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:31][CH2:30][CH2:29][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[N:6]=[C:5]2[NH:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([NH2:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 67297950HCID 67297950, compound

Product 1

HCID 67298585HCID 67298585, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The suspension of 2-(6-hydroxy-2-(pyridin-3-yl)quinazolin-4-ylamino)benzamide (50 mg, 0.14 mmol), 1-bromo-2-chloroethane (0.015 ml, 0.15 mmol), and potassium carbonate (23 mg, 0.17 mmol) in DMF (5 mL) was stirred for 3 days at room temperature. Water (10 mL) was added to the mixture and extracted with ethyl acetate (2×10 mL). The combined organic layer was washed with water (1×20 mL) and brine (1×20 mL) and was dried over MgSO4. After filtration and evaporation, the crude product was obtained, which was washed with hexane and dried to give 48 mg of 2-(6-(2-chloroethoxy)-2-(pyridin-3-yl)quinazolin-4-ylamino)benzamide as light brown solid (79%).

Workup

  1. extractionextracted with ethyl acetate (2×10 mL)
  2. washThe combined organic layer was washed with water (1×20 mL) and brine (1×20 mL)
  3. dry with materialwas dried over MgSO4
  4. filtrationAfter filtration and evaporation
  5. customthe crude product was obtained
  6. washwhich was washed with hexane
  7. customdried

Sources & evidence

ORD record
ord-65b8eb63260d4d5287163b14c4260143
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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