Hydrochloric Acid → HCID 67228167, compound

HRID 1515669Notes

Reaction equation

HRID 1515669 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:21]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([OH:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=2)=[CH:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)(=O)=O)C=CC=CC=1.[OH-].[Na+].Cl>C(O)C.C(OCC)(=O)C>[CH:23]1([CH:22]=[C:21]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([OH:37])([CH3:35])[CH3:36])=[CH:30][CH:29]=2)[C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=2)[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67227818HCID 67227818, compound

Product 1

HCID 67228167HCID 67228167, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-{4-[1-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-propan-2-ol (160 mg, 0.31 mmol) in ethanol (3 mL) and an aqueous sodium hydroxide solution (10%, 1.5 mL) was heated at reflux for 5 h. The mixture was acidified to pH 4-5 with a 2 N aqueous hydrochloric acid solution, diluted with ethyl acetate (150 mL), washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to give 2-{4-[2-cyclopentyl-1-(5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-propan-2-ol (100 mg, 86.2%) as a light yellow solid: LC/MS m/e calcd for C24H28N2O2 [M+H]+ 377.5, observed 377.2.

Workup

  1. temperatureat reflux for 5 h
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50f764032fd94d12902d14a5fadd60f9
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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