Benzenecarboximidic acid, 3-methoxy-, ethyl ester, hydrochloride → HCID 59519026, compound

HRID 1161855Notes

Reaction equation

HRID 1161855 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([C:22](=[O:31])[NH:23][CH2:24][C:25](=[O:30])[NH:26][CH:27]([CH3:29])[CH3:28])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:43]=[CH:44][CH:45]=1)[C:38](=N)OCC>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[C:17]3[C:18](=[CH:19][CH:20]=2)[N:21]=[C:38]([C:37]2[CH:43]=[CH:44][CH:45]=[C:35]([O:34][CH3:33])[CH:36]=2)[N:23]([CH2:24][C:25](=[O:30])[NH:26][CH:27]([CH3:28])[CH3:29])[C:22]3=[O:31])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 12282163Benzenecarboximidic acid, 3-methoxy-, ethyl ester, hydrochlorideHCID 67417372HCID 67417372, compound

Product 1

HCID 59519026HCID 59519026, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-{4-Amino-3-[(isopropylcarbamoylmethyl)carbamoyl]phenyl}perhydro-1,4-diazepine-1-carboxylic acid tert-butyl ester (INTERMEDIATE V.2) (300 mg, 0.69 mmol) and ethyl 3-methoxybenzimidate hydrochloride (INTERMEDIATE II.2) (298 mg, 1.38 mmol) in EtOH (6 mL) was heated at reflux temperature for 16 h. The reaction mixture was cooled, filtered and the filtrate concentrated in vacuo. The crude residue was purified by preparative HPLC to afford 4-[3-(isopropylcarbamoylmethyl)-2-(3-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-6-yl]perhydro-1,4-diazepine-1-carboxylic acid tert-butyl ester (INTERMEDIATE VII.1) (50 mg, 0.09 mmol, 13%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-09aeeba715524762bbccf20a604bc74f
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

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