Acetic Acid → {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-acetic acid

HRID 1515676Notes

Reaction equation

HRID 1515676 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:29][C:21]3=[N:22][CH:23]=[C:24](CC#N)[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:30]([OH:33])(=[O:32])[CH3:31]>Cl>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:29][C:21]3=[N:22][CH:23]=[C:24]([CH2:31][C:30]([OH:33])=[O:32])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 53251082{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-acetonitrile

Product 1

HCID 67229455{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-acetic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-acetonitrile (as prepared in Example 38, 140 mg, 0.34 mmol) in 36% hydrochloric acid (1 mL) and acetic acid (5 mL) was refluxed for 2 h. The mixture was concentrated in vacuo, extracted with ethyl acetate (250 mL), washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford {2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-acetic acid (150 mg, quant.) as a light yellow solid which was used in the next step without further purification: LC/MS m/e calcd for C23H2N2O4S [M+H]+ 427.54, observed 427.0.

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationThe mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate (250 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96d95317fa0f4462a223b298217a122c
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

Loading…