HCID 67229389, compound → 3-[2-(4-methanesulfonyl-phenyl)-2-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-cyclopentanone

HRID 1515790Notes

Reaction equation

HRID 1515790 reaction equation
O1[C:5]2([CH2:9][CH2:8][CH:7]([CH2:10][CH:11]([C:22]3[NH:30][C:25]4=[N:26][CH:27]=[CH:28][CH:29]=[C:24]4[CH:23]=3)[C:12]3[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=3)[CH2:6]2)[O:4]CC1>O1CCCC1.Cl.C(OCC)(=O)C>[CH3:21][S:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:11]([C:22]2[NH:30][C:25]3=[N:26][CH:27]=[CH:28][CH:29]=[C:24]3[CH:23]=2)[CH2:10][CH:7]2[CH2:8][CH2:9][C:5](=[O:4])[CH2:6]2)=[CH:17][CH:16]=1)(=[O:19])=[O:20]

Participants

5

Reactant 1

HCID 67229389HCID 67229389, compound

Product 1

HCID 532518703-[2-(4-methanesulfonyl-phenyl)-2-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-cyclopentanoneYield 18.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-[2-(1,4-dioxa-spiro[4.4]non-7-yl)-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (80 mg, 0.18 mmol) in tetrahydrofuran (12 mL) and aqueous hydrochloric acid solution (2 N, 6 mL) was stirred at 25° C. for 5 h. The mixture was diluted with ethyl acetate (50 mL), washed with a saturated aqueous sodium bicarbonate solution (2×20 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 50% dichloromethane/ethyl acetate) afforded 3-[2-(4-methanesulfonyl-phenyl)-2-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-cyclopentanone (diastereomer 2, 13 mg, 18%) as a white solid: LC/MS m/e calcd for C21H22N2O3S [M+H]+ 383.49, observed 383.0; 1H NMR (400 MHz, CD3OD) δ ppm 8.09 (d, J=4.5 Hz, 1H), 7.87-7.94 (m, 3H), 7.60-7.66 (m, 2H), 7.03-7.10 (m, 1H), 6.44 (d, J=3.0 Hz, 1H), 4.35-4.41 (m, 1H), 3.06-3.11 (m, 3H), 2.38-2.49 (m, 1H), 2.07-2.31 (m, 5H), 1.87-1.99 (m, 1H), 1.59-1.71 (m, 1H).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution (2×20 mL), brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 50% dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-0a4460f0efc3429081a765b5cec6a02d
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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