Hydrochloric Acid → HCID 59832323, compound

HRID 269514Notes

Reaction equation

HRID 269514 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:10]=[C:11]2[C:17]([C:18](=[O:28])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:21]=3[F:27])=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1)=[O:5])C.Cl>C(O)C.C(=O)([O-])[O-].[K+].[K+]>[F:27][C:21]1[C:22]([F:26])=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][C:18]([C:17]1[C:11]2[C:12](=[N:13][CH:14]=[C:9]([CH:7]3[CH2:8][CH:6]3[C:4]([OH:5])=[O:3])[CH:10]=2)[NH:15][CH:16]=1)=[O:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59832335HCID 59832335, compound

Product 1

HCID 59832323HCID 59832323, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 11430Potassium CarbonateSolvent

Procedure

2-{3-[(2,3-Difluoro-phenyl)-acetyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-cyclopropanecarboxylic acid ethyl ester, (130 mg, 0.33 mmol, was dissolved in 1 mL ethanol and 1 mL 10% potassium carbonate solution. The mixture was heated to reflux for ˜16 hours. The reaction was then acidified with 6N HCl to a pH ˜4-5 and extracted with dichloromethane. The essentially pure 2-{3-[(2,3-Difluoro-phenyl)-acetyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-cyclopropanecarboxylic acid was used without further purification in the next step. MS ES+ 357.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for ˜16 hours
  3. extractionextracted with dichloromethane
  4. customThe essentially pure 2-{3-[(2,3-Difluoro-phenyl)-acetyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-cyclopropanecarboxylic acid was used without further purification in the next step

Sources & evidence

ORD record
ord-1715711dc49d4c28ba9a70e17c3293f0
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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