Acetic Acid → 1-Ethyl-3,3,5-trimethyl-7-{[N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]-N-(2-morpholin-4-ylmethylbenzyl)amino]methyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 68983Notes

Reaction equation

HRID 68983 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)(=O)C.[CH2:11]([N:13]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[C:17](=[O:23])[N:16]([CH3:24])[C:15]2[CH:25]=[C:26]([CH2:29][N:30]([CH2:44][C:45]3[CH:52]=[CH:51][CH:50]=[CH:49][C:46]=3[CH:47]=O)[CH2:31][CH2:32][N:33]3[CH:38]=[CH:37][C:36]4[O:39][C:40]([CH3:42])=[CH:41][C:35]=4[C:34]3=[O:43])[CH:27]=[CH:28][C:14]1=2)[CH3:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O.ClCCCl>[CH2:11]([N:13]1[C:19](=[O:20])[C:18]([CH3:21])([CH3:22])[C:17](=[O:23])[N:16]([CH3:24])[C:15]2[CH:25]=[C:26]([CH2:29][N:30]([CH2:31][CH2:32][N:33]3[CH:38]=[CH:37][C:36]4[O:39][C:40]([CH3:42])=[CH:41][C:35]=4[C:34]3=[O:43])[CH2:44][C:45]3[CH:52]=[CH:51][CH:50]=[CH:49][C:46]=3[CH2:47][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH:27]=[CH:28][C:14]1=2)[CH3:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 866704842-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)benzaldehyde

Product 1

HCID 706564441-Ethyl-3,3,5-trimethyl-7-{[N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]-N-(2-morpholin-4-ylmethylbenzyl)amino]methyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

Morpholine (0.06 ml) and acetic acid (0.1 ml) were added to a 1,2-dichloroethane solution (7 ml) of 2-({N-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)benzaldehyde (0.35 g), and the mixture was stirred for 30 minutes at room temperature. Sodium triacetoxy borohydride (0.20 g) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction liquid, followed by extraction by dichloromethane. The organic layer was dried by anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=3:2). The purified product was condensed under reduced pressure to give the title compound (0.30 g) as a white amorphous solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionfollowed by extraction by dichloromethane
  3. dry with materialThe organic layer was dried by anhydrous sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=3:2)
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-8521235ab2164157b2eed8381cd6ae6a
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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