Sodium Hydroxide → 10-bromo-5-(5-hydroxymethyl-3-pyridylmethyloxy)-2-(3-pyridylmethyl)-3H-pyrido[3,2,1-kl]phenothiazin-3-one

HRID 1016311Notes

Reaction equation

HRID 1016311 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][O:13][C:14]2[CH:15]=[C:16]3[C:25]4=[C:26]([C:28](=[O:38])[C:29]([CH2:31][C:32]5[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=5)=[CH:30][N:24]4[C:23]4[CH:22]=[C:21]([Br:39])[CH:20]=[CH:19][C:18]=4[S:17]3)[CH:27]=2)[CH:9]=[N:10][CH:11]=1)(=O)C.[OH-].[Na+]>CO.O>[Br:39][C:21]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:25]4=[C:26]([C:28](=[O:38])[C:29]([CH2:31][C:32]5[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=5)=[CH:30][N:24]4[C:23]=2[CH:22]=1)[CH:27]=[C:14]([O:13][CH2:12][C:8]1[CH:9]=[N:10][CH:11]=[C:6]([CH2:5][OH:4])[CH:7]=1)[CH:15]=3

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 184065815-(5-acetoxymethyl-3-pyridylmethyloxy)-10-bromo-2-(3-pyridylmethyl)-3H-pyrido[3,2,1-kl]phenothiazin-3-one

Product 1

HCID 1202110910-bromo-5-(5-hydroxymethyl-3-pyridylmethyloxy)-2-(3-pyridylmethyl)-3H-pyrido[3,2,1-kl]phenothiazin-3-oneYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound (220 mg) obtained in Example 41 was suspended in methanol(10 mL) and to the suspension was added dropwise a solution of sodium hydroxide (90 mg) in water (1 mL). The mixture was stirred at room temperature overnight. After the end of reaction, the precipitate crystals were collected by filtration and washed with methanol and ether in turns to obtain the title compound (180 mg; 91%).

Workup

  1. customAfter the end of reaction
  2. filtrationthe precipitate crystals were collected by filtration
  3. washwashed with methanol and ether in turns

Sources & evidence

ORD record
ord-e497204283aa4949b04f6a4da854ebe6
Source dataset
uspto-grants-2002_11
Patent number
US06476021B1

Reaction notes

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