Acetic Acid → HCID 21219078, compound

HRID 1585655Notes

Reaction equation

HRID 1585655 reaction equation
[CH3:1][C:2]1[C:3]([C:8]2[CH:9]=[C:10]3[C:15](=[C:16]([NH:18][S:19]([C:22]4[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:36])[CH2:30][C:31]([O:33]CC)=[O:32])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[N:17]=2)[N:14]=[CH:13][CH:12]=[CH:11]3)=[N:4][CH:5]=[CH:6][CH:7]=1.C(O)(=O)C>[OH-].[Na+].O>[CH3:1][C:2]1[C:3]([C:8]2[CH:9]=[C:10]3[C:15](=[C:16]([NH:18][S:19]([C:22]4[CH:23]=[CH:24][C:25]([NH:28][C:29](=[O:36])[CH2:30][C:31]([OH:33])=[O:32])=[CH:26][CH:27]=4)(=[O:21])=[O:20])[N:17]=2)[N:14]=[CH:13][CH:12]=[CH:11]3)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 21219080HCID 21219080, compound

Product 1

HCID 21219078HCID 21219078, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Heat a stirred suspension of ethyl 3-[[4-[[[6-(3-methyl-2-pyridinyl)-1,7-naphthyridin-8-yl]amino]sulfonyl]-phenyl]amino]-3-oxopropanoate (387 mg, 0.765 mmol) in 0.125 N aqueous sodium hydroxide solution at 60° C. for 2 hours. Allow the reaction solution to cool to room temperature, and adjust the pH of the solution to 4-5 by the dropwise addition of glacial acetic acid. Dilute with water (50 mL) and filter. Triturate the isolate solid with methanol (1.5 mL), dilute with water (50 mL), filter and vacuum dry to obtain the title compound as a monohydrate, C23H19N5O5S.H2O, mp 163-164° C. (dec). FABMS: MH+ 478 (100%).

Workup

  1. temperatureHeat
  2. filtrationfilter
  3. customTriturate the isolate solid with methanol (1.5 mL)
  4. additiondilute with water (50 mL)
  5. filtrationfilter
  6. customvacuum dry

Sources & evidence

ORD record
ord-0fbeb7b2eb4d4a9cadb87cdf1caa20c3
Source dataset
uspto-grants-1999_08
Patent number
US05939431

Reaction notes

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