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Sodium hydride → 7-Bromo-4-(4-methoxybenzyl)-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-one

HRID 1362070
Notes
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Reaction equation

HRID 1362070 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([CH2:16][C:17]1[C:18]([NH2:24])=[N:19][CH:20]=[C:21]([Br:23])[CH:22]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)C.[H-].[Na+]>CS(C)=O.O>[Br:23][C:21]1[CH:20]=[N:19][C:18]2[NH:24][C:4](=[O:3])[CH2:5][N:6]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)[CH2:16][C:17]=2[CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 59456962[(2-Amino-5-bromo-pyridin-3-ylmethyl)-(4-methoxy-benzyl)amino]acetic acid ethyl ester

Product 1

HCID 594569197-Bromo-4-(4-methoxybenzyl)-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-oneYield 62%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962
Water
Solvent

Procedure

A solution of [(2-amino-5-bromo-pyridin-3-ylmethyl)-(4-methoxy-benzyl)amino]acetic acid ethyl ester (13.0 g, 31.9 mmol) in DMSO (200 mL) was treated with NaH (60% dispersion in mineral oil, 1.30 g, 32.5 mmol). After stirring at room temperature overnight, the mixture was diluted with H2O (500 mL) and a precipitate formed. The solid was isolated by filtration, washed with H2O, and dried under vacuum at 50° C. for 6.5 h to give the title compound (7.16 g, 62%) as a tan powder: MS (ESI) m/e 362 (M+H)+.

Workup

  1. customa precipitate formed
  2. customThe solid was isolated by filtration
  3. washwashed with H2O
  4. customdried under vacuum at 50° C. for 6.5 h

Sources & evidence

ORD record
ord-b9fad6b06e754d6abe8f5e9671c3a323
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879872B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes