Hydrogen chloride-ethyl acetate → N-{[3-(aminomethyl)phenyl]methyl}-6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxamide hydrochloride

HRID 606474Notes

Reaction equation

HRID 606474 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([NH:15][CH2:16][C:17]1[CH:18]=[C:19]([CH2:23][NH:24]C(=O)OC(C)(C)C)[CH:20]=[CH:21][CH:22]=1)=[O:14])[NH:7][C:6]2=[O:32])#[N:2].[ClH:33].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:33].[NH2:24][CH2:23][C:19]1[CH:18]=[C:17]([CH2:16][NH:15][C:13]([C:8]2[NH:7][C:6](=[O:32])[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=3)[N:9]=2)=[O:14])[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 1360544931,1-Dimethylethyl {[3-({[(6-cyano-4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)phenyl]methyl}carbamate

Product 1

HCID 136380963N-{[3-(aminomethyl)phenyl]methyl}-6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxamide hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of 1,1-dimethylethyl {[3-({[(6-cyano-4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)phenyl]methyl}carbamate obtained in Reference Example 46 (2.14 g, 4.94 mmol) in ethyl acetate (5 mL) was added 4N hydrogen chloride/ethyl acetate (60 mL), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from toluene. The obtained crude crystals were suspended in ethyl acetate, and the suspension was stirred under heating for 3 hr to give the title compound as a white powder (1.86 g, 99%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from toluene
  3. customThe obtained crude crystals
  4. stirringthe suspension was stirred
  5. temperatureunder heating for 3 hr

Sources & evidence

ORD record
ord-84c86696b93442a5b1551e9a73cf5c64
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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