Water → HCID 178500539, compound

HRID 1091524Notes

Reaction equation

HRID 1091524 reaction equation
Cl.[OH:2][C:3]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[CH:4][C:5]1[N:14]2[CH2:15][CH2:16][N:17]=[C:13]2[C:12]2[CH:11]=[CH:10][C:9]([OH:18])=[C:8]([O:19][CH3:20])[C:7]=2[N:6]=1.Cl[CH:28]([CH2:33][CH3:34])[C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[OH:2][C:3]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[CH:4][C:5]1[N:14]2[CH2:15][CH2:16][N:17]=[C:13]2[C:12]2[CH:11]=[CH:10][C:9]([O:18][CH2:34][CH2:33][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:8]([O:19][CH3:20])[C:7]=2[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 123415Methyl 2-chlorobutanoateHCID 178493830HCID 178493830, compound

Product 1

HCID 178500539HCID 178500539, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-(2-hydroxy-2-pyridin-3-ylvinyl)-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-ol hydrochloride (Example 1-4) 50.4 mg (0.14 mmol), methyl chlorobutyrate 22.2 mg (0.16 mmol) and potassium carbonate 186.9 mg (1.35 mmol) in N,N-dimethylformamide 1 mL was stirred at 120° C. for 4 hours. The reaction mixture was poured into water and extracted into dichloromethane. The organic layer was washed with brine, dried over MgSO4, filtrated and the solvent was evaporated. The residue was washed by diethyl ether to give the title compound 35.0 mg as yellow solid. Yield 59.3%.

Workup

  1. extractionextracted into dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltrated
  5. customthe solvent was evaporated
  6. washThe residue was washed by diethyl ether

Sources & evidence

ORD record
ord-e2848dc7097544ba93de898b87cd16b4
Source dataset
uspto-grants-2012_03
Patent number
US08129386B2

Reaction notes

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