Trimethylamine → (2-{7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yloxycarbonylamino}-ethyl)-trimethyl-ammonium chloride

HRID 1519478Notes

Reaction equation

HRID 1519478 reaction equation
[CH3:1][N:2]([CH3:4])[CH3:3].[Cl:5][C:6]1[CH:42]=[CH:41][C:9]2[N:10]([C:22](=[O:40])[C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH3:37])=[CH:25][C:24]=3[CH3:39])[CH2:11][CH2:12][CH2:13][CH:14]([O:15][C:16](=[O:21])[NH:17][CH2:18][CH2:19]Cl)[C:8]=2[CH:7]=1>C(O)C>[Cl-:5].[Cl:5][C:6]1[CH:42]=[CH:41][C:9]2[N:10]([C:22](=[O:40])[C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH3:37])=[CH:25][C:24]=3[CH3:39])[CH2:11][CH2:12][CH2:13][CH:14]([O:15][C:16]([NH:17][CH2:18][CH2:19][N+:2]([CH3:4])([CH3:3])[CH3:1])=[O:21])[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 86708937{7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl} (2-chloroethyl)carbamate

Product 1

HCID 66733336(2-{7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yloxycarbonylamino}-ethyl)-trimethyl-ammonium chloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
170 °C

Procedure

Trimethylamine (30% solution, 0.5 ml) was added to an ethanol solution (10 ml) of {7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl}(2-chloroethy)carbamate (330 mg), and the mixture was heated at 170° C. for 15 minutes (microwave reactor). After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. To the residue was added ethyl acetate, and the resulted precipitates were collected by filtration and dried to obtain 120 mg of (2-{7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yloxycarbonylamino}-ethyl)-trimethyl-ammonium chloride as white powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate
  4. customthe resulted precipitates
  5. filtrationwere collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-67a158e7e0af4212bfc2efd29c842dd4
Source dataset
uspto-grants-2015_07
Patent number
US09073868B2

Reaction notes

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