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Hydrochloric Acid → HCID 23119447, compound

HRID 1819506
Notes
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Reaction equation

HRID 1819506 reaction equation
C([O:3][C:4](=[O:35])/[C:5](/[CH3:34])=[CH:6]/[C:7]1[C:12]([F:13])=[CH:11][C:10]([C:14](=[O:32])[NH:15][C:16]2[S:17][C:18]3[CH2:28][O:27][C:26]4[C:25]([CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=[CH:22][C:21]=4[C:19]=3[N:20]=2)=[CH:9][C:8]=1[F:33])C.CO.[OH-].[Na+].Cl>C1COCC1>[F:33][C:8]1[CH:9]=[C:10]([C:14](=[O:32])[NH:15][C:16]2[S:17][C:18]3[CH2:28][O:27][C:26]4[C:25]([CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=[CH:22][C:21]=4[C:19]=3[N:20]=2)[CH:11]=[C:12]([F:13])[C:7]=1/[CH:6]=[C:5](\[CH3:34])/[C:4]([OH:35])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 57887231HCID 57887231, compound

Product 1

HCID 23119447HCID 23119447, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-[2,6-difluoro-4-(6-isopropyl-4H-chromeno[4,3-d]thiazol-2-ylcarbamoyl)phenyl]-2-methylacrylic acid ethyl ester (620 mg) was dissolved in THF (2 mL), methanol (2 ml), and 2N sodium hydroxide aqueous solution (2 mL), and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, and brine, dried over magnesium sulfate, and evaporated. The residue was recrystallized from ethyl acetate to obtain the compound (A1309) 460 mg.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was recrystallized from ethyl acetate
  6. customto obtain the compound (A1309) 460 mg

Sources & evidence

ORD record
ord-f8d86173912642c5bebdb062f767b26c
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601746B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes