Dimethylamine → (2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzenesulfonyl}-ethyl)-dimethyl-amine

HRID 1515819Notes

Reaction equation

HRID 1515819 reaction equation
[CH:1]1([CH2:6][CH:7]([C:19]2[NH:27][C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]=[CH2:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][NH:29][CH3:30].CO>>[CH:1]1([CH2:6][CH:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH2:18][N:29]([CH3:30])[CH3:28])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[C:19]2[NH:27][C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 887MethanolHCID 672293482-[2-cyclopentyl-1-(4-ethenesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 53252184(2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzenesulfonyl}-ethyl)-dimethyl-amineYield 12%

Conditions

Temperature
25 °C

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-ethenesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.39 mmol) and dimethylamine solution in methanol (2 M, 3 ml, 6 mmol) was stirred at 25° C. for 20 min. 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 (2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-benzenesulfonyl}-ethyl)-dimethyl-amine (20 mg, 12%) as a white solid: LC/MS m/e calcd for C24H31N3O2S [M+H]+ 426.60, observed 426.1; 1H NMR (400 MHz, CD3OD) δ ppm 8.08 (d, J=4.5 Hz, 1H), 7.83-7.91 (m, 2H), 7.61 (d, J=8.1 Hz, 1H), 7.04 (dd, J=7.6, 5.1 Hz, 1H), 6.39 (s, 1H), 5.49 (s, 7H), 4.32 (t, J=7.8 Hz, 1H), 3.33-3.39 (m, 2H), 2.64-2.71 (m, 1H), 2.21-2.33 (m, 1H), 2.07-2.19 (m, 5H), 1.59-1.86 (m, 4H), 1.43-1.59 (m, 2H), 1.15-1.34 (m, 2H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-7c7165fd80a44ca19ec47fe913c34244
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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