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-(pyridin-4-ylmethyl)amino}methyl)-1,5-dihydro benzo[b][1,4]diazepine-2,4-dione

HRID 68962Notes

Reaction equation

HRID 68962 reaction equation
O[CH:2](O)[CH2:3][N:4]1[CH:9]=[CH:8][C:7]2[O:10][C:11]([CH3:13])=[CH:12][C:6]=2[C:5]1=[O:14].C(O)(=O)C.[CH2:20]([N:22]1[C:28](=[O:29])[C:27]([CH3:31])([CH3:30])[C:26](=[O:32])[N:25]([CH3:33])[C:24]2[CH:34]=[C:35]([CH2:38][NH:39][CH2:40][C:41]3[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=3)[CH:36]=[CH:37][C:23]1=2)[CH3:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:20]([N:22]1[C:28](=[O:29])[C:27]([CH3:31])([CH3:30])[C:26](=[O:32])[N:25]([CH3:33])[C:24]2[CH:34]=[C:35]([CH2:38][N:39]([CH2:2][CH2:3][N:4]3[CH:9]=[CH:8][C:7]4[O:10][C:11]([CH3:13])=[CH:12][C:6]=4[C:5]3=[O:14])[CH2:40][C:41]3[CH:42]=[CH:43][N:44]=[CH:45][CH:46]=3)[CH:36]=[CH:37][C:23]1=2)[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 669600005-(2,2-Dihydroxyethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-oneHCID 706567911-Ethyl-3,3,5-trimethyl-7-{[(pyridin-4-ylmethyl)amino]methyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 706565031-ethyl-3,3,5-trimethyl-7-({N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]-N-(pyridin-4-ylmethyl)amino}methyl)-1,5-dihydro benzo[b][1,4]diazepine-2,4-dioneYield 86.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-(2,2-Dihydroxyethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one (0.21 g) and acetic acid (0.1 ml) were added to a 1,2-dichloroethane solution (15 ml) of 1-ethyl-3,3,5-trimethyl-7-{[(pyridin-4-ylmethyl)amino]methyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.38 g), and the mixture was stirred for 30 minutes at room temperature. Sodium triacetoxy borohydride (0.42 g) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→4:1). The purified product was condensed under reduced pressure, and the residue was recrystallized from ether to give the title compound (0.47 g) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customcondensed under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→4:1)
  4. customcondensed under reduced pressure
  5. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-c5ab8519a3914a7cb0a50370094247d7
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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