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

HRID 1939627Notes

Reaction equation

HRID 1939627 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-1b682796b6724d32b7fab62666effc95
Source dataset
uspto-grants-1997_12
Patent number
US05696260

Reaction notes

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