Sodium triacetoxyborohydride → 1-ethyl-3,3,5-trimethyl-7-(4-{N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]-N-(pyridin-4-ylmethyl)amino}butyl)-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione dihydrochloride

HRID 68957Notes

Reaction equation

HRID 68957 reaction equation
[CH3:1][C:2]1[O:10][C:9]2[CH:8]=[CH:7][N:6]([CH2:11][CH:12]=O)[C:5](=[O:14])[C:4]=2[CH:3]=1.[CH2:15]([N:17]1[C:23](=[O:24])[C:22]([CH3:26])([CH3:25])[C:21](=[O:27])[N:20]([CH3:28])[C:19]2[CH:29]=[C:30]([CH2:33][CH2:34][CH2:35][CH2:36][NH:37][CH2:38][C:39]3[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=3)[CH:31]=[CH:32][C:18]1=2)[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OC(=O)C)C.[ClH:65]>C(OCC)(=O)C.ClCCCl.C(O)(=O)C>[ClH:65].[ClH:65].[CH2:15]([N:17]1[C:23](=[O:24])[C:22]([CH3:26])([CH3:25])[C:21](=[O:27])[N:20]([CH3:28])[C:19]2[CH:29]=[C:30]([CH2:33][CH2:34][CH2:35][CH2:36][N:37]([CH2:12][CH2:11][N:6]3[CH:7]=[CH:8][C:9]4[O:10][C:2]([CH3:1])=[CH:3][C:4]=4[C:5]3=[O:14])[CH2:38][C:39]3[CH:40]=[CH:41][N:42]=[CH:43][CH:44]=3)[CH:31]=[CH:32][C:18]1=2)[CH3:16]

Participants

8

Reactant 4

HCID 5049666Sodium triacetoxyborohydrideHCID 21866389Hydrogen chloride-ethyl acetateHCID 706567041-Ethyl-3,3,5-trimethyl-7-{4-[(pyridin-4-ylmethyl)amino]butyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneHCID 86670479(2-Methyl-4-oxo-4H-furo[3,2-c]pyridin 5-yl)acetaldehyde

Product 1

HCID 706566451-ethyl-3,3,5-trimethyl-7-(4-{N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]-N-(pyridin-4-ylmethyl)amino}butyl)-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione dihydrochloride

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-Methyl-4-oxo-4H-furo[3,2-c]pyridin 5-yl)acetaldehyde (0.18 g) and acetic acid (0.1 ml) were added to a 1,2-dichloroethane solution (5 ml) of 1-ethyl-3,3,5-trimethyl-7-{4-[(pyridin-4-ylmethyl)amino]butyl}-1,5-dihydrobenzo[b][1,4]diazepine 2,4-dione (0.38 g). The mixture was stirred for 30 minutes at room temperature. sodium triacetoxyborohydride (0.32 g) was added to the mixture, 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→9:1). The purified product was condensed under reduced pressure. A 6N-hydrogen chloride ethyl acetate solution (1.0 ml) was added to an ethyl acetate solution (20 ml) of the residue, and the liquid was stirred at room temperature. The precipitated insoluble matter was separated, washed with ethyl acetate, and dried to give the title compound (0.43 g) as a white solid.

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→9:1)
  4. customcondensed under reduced pressure
  5. stirringthe liquid was stirred at room temperature
  6. customThe precipitated insoluble matter was separated
  7. washwashed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-b42212217339456baee78b5a6ff9fa67
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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