Sodium hydride → 7-Bromo-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one

HRID 1362080Notes

Reaction equation

HRID 1362080 reaction equation
C([O:3][C:4](=O)[CH2:5][NH:6][CH2:7][C:8]1[C:9]([NH2:15])=[N:10][CH:11]=[C:12]([Br:14])[CH:13]=1)C.[H-].[Na+]>CS(C)=O.O>[Br:14][C:12]1[CH:11]=[N:10][C:9]2[NH:15][C:4](=[O:3])[CH2:5][NH:6][CH2:7][C:8]=2[CH:13]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 59456921Ethyl 2-((2-amino-5-bromopyridin-3-yl)methylamino)acetate

Product 1

HCID 594569547-Bromo-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-oneYield 72.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of [(2-amino-5-bromo-pyridin-3-ylmethyl)amino]acetic acid ethyl ester (1.79 g, 6.21 mmol) in DMSO (70 mL) was treated with NaH (60% dispersion in mineral oil, 0.25 g, 6.2 mmol). After stirring at room temperature for 27 h, the mixture was diluted with H2O (300 mL), and extracted then with EtOAc (4×150 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 to give the title compound (1.09 g, 72%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 8.26 (d, J=2.1 Hz, 1H), 8.17 (s, 1H), 7.54 (d, J=1.9 Hz, 1H), 4.03 (s, 2H), 3.93 (s, 2H), 1.85 (br s, 1H); MS (ESI) m/e 242 (M+H)+.

Workup

  1. extractionextracted
  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

Sources & evidence

ORD record
ord-2a5b28fd401748fdb04ddfd6b64306c6
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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