Potassium Carbonate → HCID 67155919, compound

HRID 2196698Notes

Reaction equation

[CH:1]1([C:5]2[C:13]3[C:8](=[N:9][CH:10]=[C:11]([NH:14][C:15](=[O:31])[C:16]4[C:21]([F:22])=[CH:20][CH:19]=[C:18]([NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25])[C:17]=4[F:30])[CH:12]=3)[N:7](S(C3C=CC=CC=3)(=O)=O)[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO.CCOC(C)=O>[CH:1]1([C:5]2[C:13]3[C:8](=[N:9][CH:10]=[C:11]([NH:14][C:15](=[O:31])[C:16]4[C:21]([F:22])=[CH:20][CH:19]=[C:18]([NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:25])=[O:26])[C:17]=4[F:30])[CH:12]=3)[NH:7][CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

Conditions

Temperature: 60 °C

Procedure

N-(3-Cyclobutyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide was dissolved in methanol (1 mL), and aqueous 2M potassium carbonate (1 mL) was added. The mixture was warmed to 60° C. for 1 hour. The mixture was then diluted with EtOAc, washed with 10% aqueous citric acid (1×), water (1×), dried over sodium sulfate and concentrated. Prep TLC (2×0.5 mm plates, 7% MeOH/DCM as the eluant) afforded N-(3-cyclobutyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (15%). 1H NMR (400 MHz, DMSO-d6) δ 11.37 (br s, 1H), 10.82 (br s, 1H), 9.78 (br s, 1H), 8.31-8.38 (m, 2H), 7.49-7.58 (m, 1H), 7.20-7.34 (m, 2H), 3.62-3.71 (m, 1H), 3.07-3.14 (m, 2H), 2.30-2.41 (m, 2H), 2.14-2.22 (m, 2H), 1.97-2.08 (m, 1H), 1.85-1.94 (m, 1H), 1.71-1.81 (m, 2H), 0.96-1.02 (m, 3H); m/z (APCI-pos) M+1=449.1.

Workup

washwashed with 10% aqueous citric acid (1×), water (1×)
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-1b957d06905b44ee8d68e4ae9cec8a61
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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