Triethylamine → 1-Ethyl-3,3,5-trimethyl-7-{2-[(pyridin-4-ylmethyl)amino]ethyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 68959Notes

Reaction equation

HRID 68959 reaction equation
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1.Cl.[NH2:17][CH2:18][CH2:19][C:20]1[CH:37]=[CH:36][C:23]2[N:24]([CH2:34][CH3:35])[C:25](=[O:33])[C:26]([CH3:32])([CH3:31])[C:27](=[O:30])[N:28]([CH3:29])[C:22]=2[CH:21]=1.[BH4-].[Na+]>CO>[CH2:34]([N:24]1[C:25](=[O:33])[C:26]([CH3:32])([CH3:31])[C:27](=[O:30])[N:28]([CH3:29])[C:22]2[CH:21]=[C:20]([CH2:19][CH2:18][NH:17][CH2:14][C:11]3[CH:10]=[CH:9][N:8]=[CH:13][CH:12]=3)[CH:37]=[CH:36][C:23]1=2)[CH3:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 70656066HCID 70656066, compound

Product 1

HCID 706567551-Ethyl-3,3,5-trimethyl-7-{2-[(pyridin-4-ylmethyl)amino]ethyl}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (0.1 ml) and 4-pyridine carbaldehyde (0.094 ml) were added to a methanol solution (10 ml) of 7-(2-aminoethyl)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine 2,4-dione hydrochloride (0.26 g). The mixture was stirred at room temperature for 1 hour. Sodium borohydride (0.11 g) was added, and the mixture was further stirred at room temperature overnight. The reaction liquid was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→3:2). The purified product was condensed under reduced pressure to give the title compound (0.21 g) as a colorless oily matter.

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. customThe reaction liquid
  3. customcondensed under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→3:2)
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-c841b8260f5c4d29a4dbebc2d95fbf67
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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