Water → 9-Carboethoxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one

HRID 849636Notes

Reaction equation

HRID 849636 reaction equation
[NH2:1][C:2]1[C:11]2[CH2:10][CH:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8][CH2:7][C:6]=2[NH:5][C:4](=[O:17])[N:3]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25](=O)[CH2:26]Br.O>CN(C=O)C>[C:12]([CH:9]1[CH2:8][CH2:7][C:6]2[NH:5][C:4](=[O:17])[N:3]3[CH:26]=[C:25]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[F:18])[N:1]=[C:2]3[C:11]=2[CH2:10]1)([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 27374492-Bromo-2'-fluoroacetophenoneHCID 152840934-Amino-6-carboethoxy-5,6,7,8-tetrahydro-2(1H)-quinazolinone

Product 1

HCID 99285709-Carboethoxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-Amino-6-carboethoxy-5,6,7,8-tetrahydro-2(1H)-quinazolinone (262 mg) and 2'-fluoro-bromoacetophenone (217 mg) in dry DMF (10 mL) was refluxed under nitrogen for 1.5 h. The solution was cooled and 40 mL water is added. The precipitate was collected and washed successively with 10 mL of methanol and 20 mL hot ethyl acetate to yield 9-Carboethoxy-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one (Compound 1), m.p. 257-277° C.

Workup

  1. temperatureThe solution was cooled
  2. customThe precipitate was collected
  3. washwashed successively with 10 mL of methanol and 20 mL hot ethyl acetate

Sources & evidence

ORD record
ord-a6d385734dbd4388a36656ddcbf8c012
Source dataset
uspto-grants-2000_01
Patent number
US06013799

Reaction notes

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