Methanol → HCID 70657140, compound

HRID 68985Notes

Reaction equation

HRID 68985 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14].CO.[CH2:17]([N:19]1[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[C:23](=[O:29])[N:22]([CH3:30])[C:21]2[CH:31]=[C:32]([CH:35]=O)[CH:33]=[CH:34][C:20]1=2)[CH3:18].[BH4-].[Na+]>O>[CH2:17]([N:19]1[C:25](=[O:26])[C:24]([CH3:27])([CH3:28])[C:23](=[O:29])[N:22]([CH3:30])[C:21]2[CH:31]=[C:32]([CH2:35][NH:1][CH2:2][CH2:3][N:4]3[CH:13]=[CH:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]3=[O:14])[CH:33]=[CH:34][C:20]1=2)[CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 669605002-(2-Aminoethyl)-2H-isoquinolin-1-oneHCID 866704761-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde

Product 1

HCID 70657140HCID 70657140, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(2-Aminoethyl)-2H-isoquinolin-1-one (1.0 g) was added to a methanol solution (15 ml) of 1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde (1.46 g). The mixture was stirred for 0.5 hours at room temperature. Sodium borohydride (0.23 g) was added to the mixture, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction using dichloromethane. The organic layer was washed with water and saturated saline, dried with magnesium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→8:2). The purified product was condensed under reduced pressure to give the title compound (1.92 g) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionfollowed by extraction
  3. washThe organic layer was washed with water and saturated saline
  4. dry with materialdried with magnesium sulfate, and condensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→8:2)
  6. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-af15ea9e12f042afa0a83a3398039a66
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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