Sodium Hydroxide → 10-Methyl-8-[1-(1-methyl-1h-pyrazol-3-ylcarbamoyl)-2-(3-oxo-cyclopentyl)-ethyl]-5,5-dioxo-5,10-dihydrophenothiazin-3-carboxylic acid

HRID 14995Notes

Reaction equation

HRID 14995 reaction equation
[CH3:1][N:2]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([O:18]CC)=[O:17])=[CH:11][C:10]=2[S:9](=[O:22])(=[O:21])[C:8]2[C:3]1=[CH:4][C:5]([CH:23]([C:31](=[O:39])[NH:32][C:33]1[CH:37]=[CH:36][N:35]([CH3:38])[N:34]=1)[CH2:24][CH:25]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26]1)=[CH:6][CH:7]=2.[OH-].[Na+]>CO>[CH3:1][N:2]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][C:10]=2[S:9](=[O:21])(=[O:22])[C:8]2[C:3]1=[CH:4][C:5]([CH:23]([C:31](=[O:39])[NH:32][C:33]1[CH:37]=[CH:36][N:35]([CH3:38])[N:34]=1)[CH2:24][CH:25]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26]1)=[CH:6][CH:7]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58024214ethyl 10-methyl-8-[1-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2-(3-oxocyclopentyl)ethyl]-5,5-dioxo-5,10-dihydrophenothiazine-3-carboxylate

Product 1

HCID 6723766810-Methyl-8-[1-(1-methyl-1h-pyrazol-3-ylcarbamoyl)-2-(3-oxo-cyclopentyl)-ethyl]-5,5-dioxo-5,10-dihydrophenothiazin-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

260 mg of ethyl 10-methyl-8-[1-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2-(3-oxocyclopentyl)ethyl]-5,5-dioxo-5,10-dihydrophenothiazine-3-carboxylate are suspended in 10 ml of methanol, and 1.64 ml of a 2 M NaOH solution are added. The reaction mixture is heated at the boil under reflux for one hour. The methanol is removed under reduced pressure and the reaction mixture is adjusted to pH 4 by addition of concentrated hydrochloric acid. The mixture is extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases are dried over MgSO4 and then concentrated under reduced pressure. This gives 155 mg of 10-methyl-8-[1-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2-(3-oxocyclopentyl)ethyl]-5,5-dioxo-5,10-dihydrophenothiazine-3-carboxylic acid.

Workup

  1. temperatureThe reaction mixture is heated at the boil
  2. temperatureunder reflux for one hour
  3. customThe methanol is removed under reduced pressure
  4. additionthe reaction mixture is adjusted to pH 4 by addition of concentrated hydrochloric acid
  5. extractionThe mixture is extracted three times with in each case 100 ml of ethyl acetate
  6. dry with materialThe combined organic phases are dried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-524e663e80df4743996235ecdb96ba50
Source dataset
uspto-grants-2010_06
Patent number
US07732440B2

Reaction notes

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