Trifluoroacetic acid → 1-Ethyl-3,3,5-trimethyl-7-{[(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-ylmethyl)amino]methyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 1504154Notes

Reaction equation

HRID 1504154 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[N:14]([CH2:28][C:29]1[CH:46]=[CH:45][C:32]2[N:33]([CH2:43][CH3:44])[C:34](=[O:42])[C:35]([CH3:41])([CH3:40])[C:36](=[O:39])[N:37]([CH3:38])[C:31]=2[CH:30]=1)[CH2:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][C:22](=[O:27])[N:23]2[CH3:26])=[CH:18][CH:17]=1)(C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:43]([N:33]1[C:34](=[O:42])[C:35]([CH3:40])([CH3:41])[C:36](=[O:39])[N:37]([CH3:38])[C:31]2[CH:30]=[C:29]([CH2:28][NH:14][CH2:15][C:16]3[CH:25]=[C:24]4[C:19]([CH2:20][CH2:21][C:22](=[O:27])[N:23]4[CH3:26])=[CH:18][CH:17]=3)[CH:46]=[CH:45][C:32]1=2)[CH3:44]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 70656576HCID 70656576, compound

Product 1

HCID 706566161-Ethyl-3,3,5-trimethyl-7-{[(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-ylmethyl)amino]methyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (43.2 mg) was added to a dichloromethane solution (5 ml) of N-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-ylmethyl)carbamic acid tert-butyl ester (208 mg), and the mixture was stirred at room temperature overnight. A saturated sodium bicarbonate solution was added to the reaction mixture, followed by extraction using dichloromethane, and condensed under reduced pressure to give the title compound(148 mg) as a white amorphous.

Workup

  1. extractionfollowed by extraction
  2. customdichloromethane, and condensed under reduced pressure

Sources & evidence

ORD record
ord-e05af4c789474571a0a2a5028ddf4a0c
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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