Sodium hydride → 7-Bromo-4-(2-morpholin-4-yl-ethyl)-1,3,4,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-2-one

HRID 1362076Notes

Reaction equation

HRID 1362076 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([CH2:14][C:15]1[C:16]([NH2:22])=[N:17][CH:18]=[C:19]([Br:21])[CH:20]=1)[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[H-].[Na+]>CS(C)=O.O>[Br:21][C:19]1[CH:18]=[N:17][C:16]2[NH:22][C:3](=[O:2])[CH2:4][N:5]([CH2:6][CH2:7][N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH2:14][C:15]=2[CH:20]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 59456951[(2-Amino-5-bromo-pyridin-3-ylmethyl)-(2-morpholin-4-yl-ethyl)amino]acetic acid methyl ester

Product 1

HCID 594569787-Bromo-4-(2-morpholin-4-yl-ethyl)-1,3,4,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-2-oneYield 76.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of [(2-amino-5-bromo-pyridin-3-ylmethyl)-(2-morpholin-4-yl-ethyl)amino]acetic acid methyl ester (0.34 g, 0.88 mmol) in DMSO (10 mL) was treated with NaH (60% dispersion in mineral oil, 35 mg, 0.88 mmol). After stirring at room temperature overnight, the mixture was diluted with H2O (20 mL), and then extracted with EtOAc (4×50 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (50 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. The resulting pale yellow oil was purified by flash column chromatography (silica gel, CH2Cl2,/MeOH, 97:3 to 90:10) to give the title compound (0.24 g, 57%) as an off-white solid: MS (ESI) m/e 355 (M+H)+.

Workup

  1. extractionextracted with EtOAc (4×50 mL)
  2. washThe combined organic layers were washed with H2O (3×50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe resulting pale yellow oil was purified by flash column chromatography (silica gel, CH2Cl2,/MeOH, 97:3 to 90:10)

Sources & evidence

ORD record
ord-be617b5a2e4d462fa6a367ca2ca5f41f
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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