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

HRID 633965Notes

Reaction equation

HRID 633965 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([CH2:10][N:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH2:12][C:13](OC)=[O:14])=[CH:8][C:7]([Br:26])=[CH:6][N:5]=1.O>CS(C)=O>[Br:26][C:7]1[CH:6]=[N:5][C:4]2[NH:3][C:13](=[O:14])[CH2:12][N:11]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH2:10][C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 67154556Methyl 2-(((2-amino-5-bromopyridin-3-yl)methyl)(4-methoxybenzyl)amino)acetate

Product 1

HCID 594569197-Bromo-4-(4-methoxybenzyl)-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-oneYield 63%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (60% in oil, 140 mg, 3.40 mmol) was added to a solution of methyl 2-(((2-amino-5-bromopyridin-3-yl)methyl)(4-methoxybenzyl)amino)acetate (1.05 g, 2.66 mmol) in DMSO (17 mL) at room temperature. The reaction mixture was stirred overnight then diluted by addition of water (45 mL). After 2 hours stirring at room temperature, the reaction mixture was filtered. The resulting solid was dried under high vacuum to give the title compound as a yellow solid (600 mg, 63%) 1H NMR (DMSO-d6, 400 MHz): δ (ppm): 10.37 (s, 1H), 8.37 (s, 1H), 7.88 (s, 1H), 7.19 (d, J=8.4 Hz, 2H), 6.89 (d, J=8.4 Hz, 2H), 3.81 (s, 2H), 3.75 (s, 3H), 3.62 (s, 2H), 3.39 (s, 2H).

Workup

  1. stirringAfter 2 hours stirring at room temperature
  2. filtrationthe reaction mixture was filtered
  3. customThe resulting solid was dried under high vacuum

Sources & evidence

ORD record
ord-498485f48ad24327b7cf8088778a5d56
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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