Water → HCID 58574526, compound

HRID 1619414Notes

Reaction equation

HRID 1619414 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([C:13](Cl)=[O:14])=[CH:8][CH:9]=2)[N:4]=[CH:3]1.[S:16]1[CH:20]=[CH:19][N:18]=[C:17]1[NH2:21].O>C1COCC1.C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([C:13]([NH:21][C:17]3[S:16][CH:20]=[CH:19][N:18]=3)=[O:14])=[CH:8][CH:9]=2)[N:4]=[CH:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 21552-AminothiazoleHCID 58574194HCID 58574194, compound

Product 1

HCID 58574526HCID 58574526, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-methyl-4-oxo-3,4-dihydroquinazoline-7-carbonyl chloride prepared as described in Example 22.1a was dissolved in anhydrous THF and added to a solution of thiazol-2-amine (81 mg, 0.81 mmol) in CHCl3 (10 mL). The reaction was stirred at room temperature for 30 min and then poured into water. The mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was purified by silica gel chromatography purification to provide the desired product. MS (ESI): 287 (MH+); 1H NMR (300 MHz, DMSO-d6) δ 12.95 (s, 1H), 8.46 (s, 1H), 8.38-8.37 (d, J=1.44 Hz, 1H), 8.29-8.26 (m, 1H), 8.15-8.12 (dd, J=8.36, 1.60 Hz, 1H), 7.60-7.59 (d, J=3.57 Hz, 1H), 7.33-7.32 (d, J=3.45 Hz, 1H), 3.53 (s, 3H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe crude product was purified by silica gel chromatography purification

Sources & evidence

ORD record
ord-38373e5156904ef6868c51c00e117534
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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