Methanol → 4-oxo-N-[(3-piperazin-1-ylphenyl)methyl]-3,4-dihydroquinazoline-2-carboxamide dihydrochloride

HRID 606519Notes

Reaction equation

HRID 606519 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:17]=[C:18]([N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[CH:19]=[CH:20][CH:21]=2)=[O:13])[NH:3]1.C1COCC1.CO.C(OCC)(=O)C.[ClH:48]>C(OCC)(=O)C.C(OCC)C>[ClH:48].[ClH:48].[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)[CH:17]=2)=[O:13])[NH:3]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 21866389Hydrogen chloride-ethyl acetateHCID 1360544881,1-Dimethylethyl 4-[3-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)phenyl]piperazine-1-carboxylate

Product 1

HCID 1363809654-oxo-N-[(3-piperazin-1-ylphenyl)methyl]-3,4-dihydroquinazoline-2-carboxamide dihydrochlorideYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1,1-dimethylethyl 4-[3-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)phenyl]piperazine-1-carboxylate obtained in Reference Example 115 (2.40 g, 6.86 mmol) in ethyl acetate (10 mL)-THF (50 ml)-methanol (40 mL) was added 4N hydrogen chloride-ethyl acetate (10.4 mL), and the mixture was stirred at room temperature for 4 hr, and then at 50° C. for 2 hr. Diethyl ether (about 100 mL) was added to the reaction mixture, and the precipitated solid was collected by filtration to give the title compound as a white powder (2.18 g, 97%).

Workup

  1. waitat 50° C. for 2 hr
  2. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-07c21c902cc3492c8a16e4decdddde7c
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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