HCID 67228309, compound → HCID 53251719, compound

HRID 1515778Notes

Reaction equation

HRID 1515778 reaction equation
[CH:1]1([CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=2)[C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:17]2[CH:18]=[CH:19][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:21][CH:22]=2)[C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67228309HCID 67228309, compound

Product 1

HCID 53251719HCID 53251719, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-methanesulfonamide (83 mg, 0.22 mmol) and 10% palladium on activated carbon (30 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 5 h. The mixture was cooled to room temperature, the catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated 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) afforded N-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-phenyl}-methanesulfonamide (45 mg, 54%): LC/MS m/e calcd for C21H25N3O2S [M+H]+ 384.52, observed 384.0; 1H NMR (400 MHz, CD3OD) δ ppm 8.04 (d, J=4.0 Hz, 1H), 7.85 (d, J=7.6 Hz, 1H), 7.25-7.31 (m, J=8.3 Hz, 2H), 7.14-7.21 (m, J=8.3 Hz, 2H), 7.00 (dd, J=7.7, 4.9 Hz, 1H), 6.30 (s, 1H), 4.60 (br. s., 1H), 4.13 (t, J=7.8 Hz, 1H), 2.89 (s, 3H), 2.19 (dt, J=13.7, 7.2 Hz, 1H), 2.00-2.08 (m, 1H), 1.57-1.84 (m, 5H), 1.42-1.53 (m, 2H), 1.12-1.26 (m, 2H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-1de9b0b27b91430a990e91a38f546410
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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