Water → HCID 70188122, compound

HRID 1106514Notes

Reaction equation

HRID 1106514 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[CH:13][N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30].O>N1C=CC=CC=1>[Br:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([O:1][CH2:2][C@@H:3]([NH:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[CH:13][N:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:30]

Participants

5

Reactant 3

HCID 962WaterHCID 74377Benzoyl chloride, 3-bromo-HCID 9927305HCID 9927305, compound

Product 1

HCID 70188122HCID 70188122, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (S)-4-[α-(hydroxymethyl)benzylamino]-6,7-dimethoxyquinazoline (49 mg, 0.15 mmol) in pyridine (2 ml) was added dropwise at 0-5° C. 3-bromobenzoylchloride (33 mg, 0.15 mmol). After 6 h stirring at room temperature the reaction mixture was poured into iced water and extracted with dichloromethane. The organic layer was dried and evaporated to dryness. The residue was purified by flash chromatography on silica gel using as eluant dichloromethane/methanol 95:5 to give pure title compound as a white solid in 71% yield (54 mg).

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic layer was dried
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography on silica gel using as eluant dichloromethane/methanol 95:5

Sources & evidence

ORD record
ord-60ba51a8f82f42378de285e8499a5302
Source dataset
uspto-grants-2000_05
Patent number
US06057326

Reaction notes

Loading…