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 1504131Notes

Reaction equation

HRID 1504131 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-2ea009e168004e6d80236c286f3c7230
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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