Hydrochloric Acid → HCID 69057598, compound

HRID 730427Notes

Reaction equation

HRID 730427 reaction equation
C(/[C:3](=[CH:7]\[C:8]1[N:18]([CH:19]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11]2=[N:12][C:13]([CH3:17])=[CH:14][C:15]([CH3:16])=[C:10]2[C:9]=1[C:33]#[N:34])/[C:4]([OH:6])=[O:5])C.[OH-].[Na+].O.Cl>C(O)C.C1COCC1>[C:33]([C:9]1[C:10]2[C:11](=[N:12][C:13]([CH3:17])=[CH:14][C:15]=2[CH3:16])[N:18]([CH:19]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]=1/[CH:7]=[CH:3]/[C:4]([OH:6])=[O:5])#[N:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86760955HCID 86760955, compound

Product 1

HCID 69057598HCID 69057598, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (2E)-3-{3-cyano-1-[(4-fluorophenyl)(phenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (7.40 g, 17.0 mmol) in ethanol (70 ml) and THF (80 ml) was added a 1 N aqueous sodium hydroxide solution (34ml), and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into water, neutralized with 1 N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give the objective product as a solid material. The product was recrystallized from ethyl acetate and hexane.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-16e395433d374e7a936887a426ddb984
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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