Methanol → 1-Ethyl-7-({N-(2-hydroxymethylbenzyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 68982Notes

Reaction equation

[BH4-].[Na+].CO.[CH2:5]([N:7]1[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[C:11](=[O:17])[N:10]([CH3:18])[C:9]2[CH:19]=[C:20]([CH2:23][N:24]([CH2:38][C:39]3[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=3[CH:41]=[O:42])[CH2:25][CH2:26][N:27]3[CH:32]=[CH:31][C:30]4[O:33][C:34]([CH3:36])=[CH:35][C:29]=4[C:28]3=[O:37])[CH:21]=[CH:22][C:8]1=2)[CH3:6]>O>[CH2:5]([N:7]1[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[C:11](=[O:17])[N:10]([CH3:18])[C:9]2[CH:19]=[C:20]([CH2:23][N:24]([CH2:38][C:39]3[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=3[CH2:41][OH:42])[CH2:25][CH2:26][N:27]3[CH:32]=[CH:31][C:30]4[O:33][C:34]([CH3:36])=[CH:35][C:29]=4[C:28]3=[O:37])[CH:21]=[CH:22][C:8]1=2)[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium borohydride (47 mg) were added to a methanol solution (10 ml) of 2-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)benzaldehyde (0.59 g) and the mixture was stirred for 3 hours at 0° C. Water was added to the reaction mixture, followed by extraction by ethyl acetate. The organic layer was dried by anhydrous sodium sulfate, and condensed under reduced pressure. The residue was recrystallized from ethyl acetate-ether mixture to give the title compound (0.42 g) as a pale brown white powder.

Workup

extractionfollowed by extraction by ethyl acetate
dry with materialThe organic layer was dried by anhydrous sodium sulfate, and condensed under reduced pressure
customThe residue was recrystallized from ethyl acetate-ether mixture

Sources & evidence

ORD record: ord-9fff5a03324543deac67d07fd820ecb1
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822453B2

Reaction notes

Loading…