Sodium Hydroxide → HCID 11562388, compound

HRID 2114516Notes

Reaction equation

HRID 2114516 reaction equation
C[O:2][C:3]([C:5]1[C:18]2[O:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:15]=3)[N:10]([CH:26]3[CH2:31][CH2:30][N:29]([CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:28][CH2:27]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[CH2:32]([N:29]1[CH2:28][CH2:27][CH:26]([N:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:18]=3[O:17][C:16]3[C:11]2=[CH:12][CH:13]=[C:14]([C:19](=[O:25])[N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:15]=3)[CH2:31][CH2:30]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59809532HCID 59809532, compound2×

Product 1

HCID 11562388HCID 11562388, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 10-(1-benzylpiperidin-4-yl)-7-diethylcarbamoyl-10H-phenoxazine-4-carboxylic acid methyl ester, 3l (2.92 g, 5.7 mmol) in methanol (10 mL) was added a 1N sodium hydroxide solution (5 mL), and the mixture was heated to 50° C. for 30 min. The mixture was allowed to cool to rt, the solvent was evaporated, and the residue was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA), yielding title compound 10-(1-benzylpiperidin-4-yl)-7-diethylcarbamoyl-10H-phenoxazine-4-carboxylic acid, 4l, as a TFA salt. MS m/z (MH+) 500.1

Workup

  1. temperatureto cool to rt
  2. customthe solvent was evaporated
  3. customthe residue was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA)

Sources & evidence

ORD record
ord-575bb58e4da64887af6605459fc97872
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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