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

HRID 1362119Notes

Reaction equation

HRID 1362119 reaction equation
C[O:2][C:3](=O)[C:4]([NH:7][CH2:8][C:9]1[C:10]([NH2:16])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)([CH3:6])[CH3:5].[H-].[Na+]>CS(C)=O.O>[Br:15][C:13]1[CH:12]=[N:11][C:10]2[NH:16][C:3](=[O:2])[C:4]([CH3:6])([CH3:5])[NH:7][CH2:8][C:9]=2[CH:14]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 59456940HCID 59456940, compound

Product 1

HCID 594569147-Bromo-3,3-dimethyl-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 2-[(2-amino-5-bromo-pyridin-3-ylmethyl)amino]-2-methylpropionic acid methyl ester (2.63 g, 8.71 mmol) in DMSO (100 mL) was treated with NaH (60% dispersion in mineral oil, 0.35 g, 8.7 mmol). After stirring at room temperature overnight, the mixture was diluted with H2O (200 mL) and then extracted with EtOAc (5×150 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. Purification by flash column chromatography (silica gel, CH2Cl2,/MeOH, 99:1 to 98:2) gave (0.79 g, 33%) as an off-white solid: MS (ESI) m/e 270 (M+H)+.

Workup

  1. extractionextracted with EtOAc (5×150 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
  6. customPurification by flash column chromatography (silica gel, CH2Cl2,/MeOH, 99:1 to 98:2)
  7. customgave (0.79 g, 33%) as an off-white solid

Sources & evidence

ORD record
ord-b4709b36cc5d447fbcbb663666337a9e
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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