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

HRID 1515626Notes

Reaction equation

HRID 1515626 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:34][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][CH:27]4[CH2:31][O:30]C(C)(C)[O:28]4)[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.Cl>O1CCCC1>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:34][C:21]3=[N:22][CH:23]=[C:24]([CH2:26][CH:27]([OH:28])[CH2:31][OH:30])[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 313Hydrochloric AcidHCID 67228059HCID 67228059, compound

Product 1

HCID 532505823-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propane-1,2-diolYield 41.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridine (260 mg, 0.54 mmol) and 6N HCl (1.0 mL) in tetrahydrofuran (5 mL) was heated at reflux for 1 h. The mixture was cooled to room temperature and extracted with ethyl acetate and then washed with a saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) to afford 3-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propane-1,2-diol (100 mg, 41.9%) as a white solid: LC/MS m/e calcd for C24H30N2O4S [M+H]+ 443.58, observed 443.2; 1H NMR (400 MHz, CDCl3) δ ppm 1.15 (m, 2H), 1.45 (m, 2H), 1.54-1.82 (m, 5H, H), 2.06 (m, 1H), 2.23 (m, 1H), 2.74 (dd, J=8.1, J=13.8 Hz, 1H), 2.82 (dd, J=4.8, J=13.8 Hz, 1H), 2.90 (br, 2H), 2.98 (s, 3H), 3.53 (dd, J=7.3, J=11.4 Hz, 1H), 3.68 (dd, J=3.0, J=11.4 Hz, 1H), 3.93 (m, 1H), 4.22 (t, J=7.7 Hz, 1H), 6.29 (s, 1H), 7.75 (d, J=8.3 Hz, 2H), 7.71 (s, 1H), 7.76 (s, 1H), 7.77 (d, J=8.3 Hz, 2 H), 10.82 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. extractionextracted with ethyl acetate
  4. washwashed with a saturated aqueous sodium bicarbonate solution, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-94f7797cfaa2481ea9d8a9dd5f9d778e
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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