Sodium Hydroxide → (+/-)-8-Methyl-5-(4-nitrophenyl)-7-(2-pyrimidinyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

HRID 25087Notes

Reaction equation

HRID 25087 reaction equation
S(O[CH:6]([CH3:35])[CH2:7][C:8]1[C:16]([C:17]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[N:18][NH:19][C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[CH:9]=1)(=O)(=O)C.[OH-].[Na+]>ClCCl.CO>[CH3:35][CH:6]1[CH2:7][C:8]2[CH:9]=[C:10]3[O:14][CH2:13][O:12][C:11]3=[CH:15][C:16]=2[C:17]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[N:18][N:19]1[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1317247421-{6-[(4-Nitrophenyl)-(pyrimidin-2-yl-hydrazono)-methyl]-benzo-1,3-dioxol-5-yl}-propan-2-ol mesylate

Product 1

HCID 22565487(+/-)-8-Methyl-5-(4-nitrophenyl)-7-(2-pyrimidinyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineYield 77.5%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 3.13 g (6.27 mmol) of the compound obtained in Step B, 60 ml of a 1:1 mixture of dichloromethane-methanol and 0.52 ml (6.90 mmol) of 50% sodium hydroxide solution was stirred at room for 1.5 h. After filtration the reaction mixture was concentrated, the residue was treated with water and recrystallized from three fold dimethylformamide containing 10% water to yield 1.96 g (77%) of the title compound; Mp.: 261-263° C.

Workup

  1. filtrationAfter filtration the reaction mixture
  2. concentrationwas concentrated
  3. additionthe residue was treated with water
  4. customrecrystallized from three fold dimethylformamide containing 10% water

Sources & evidence

ORD record
ord-c641818e40aa43a2ac61a768a117d1fa
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Reaction notes

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