Sodium hydride → (7-Bromo-2-oxo-1,2,3,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-4-yl)acetic acid ethyl ester

HRID 1362057Notes

Reaction equation

HRID 1362057 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([CH2:13][C:14]1[C:15]([NH2:21])=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=1)[CH2:7][C:8](OCC)=[O:9])[CH3:2].[H-].[Na+]>CS(C)=O.O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]1[CH2:13][C:14]2[CH:19]=[C:18]([Br:20])[CH:17]=[N:16][C:15]=2[NH:21][C:8](=[O:9])[CH2:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 59456979[(2-Amino-5-bromo-pyridin-3-ylmethyl)ethoxycarbonylmethyl-amino]acetic acid ethyl ester

Product 1

HCID 59456907(7-Bromo-2-oxo-1,2,3,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-4-yl)acetic acid ethyl esterYield 108.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of [(2-amino-5-bromo-pyridin-3-ylmethyl)ethoxycarbonylmethyl-amino]-acetic acid ethyl ester (6.52 g, 17.4 mmol) in DMSO (170 mL) was treated with NaH (0.70 g, 17.5 mmol). After stirring at room temperature overnight, the mixture was diluted with H2O (300 mL) and extracted with EtOAc (4×200 mL). The combined organic layers were washed with H2O (3×100 mL) and brine (100 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo to give the title compound (6.18 g, quantitative) as an off-white solid: MS (ESI) m/e 328 (M+H)+.

Workup

  1. extractionextracted with EtOAc (4×200 mL)
  2. washThe combined organic layers were washed with H2O (3×100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fee84b778b1b4b1c8b80d7360241b4c5
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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