Piperidine → HCID 44223175, compound

HRID 2196652Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([NH:20][C:21](=[O:37])[C:22]3[C:27]([F:28])=[CH:26][CH:25]=[C:24]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[C:23]=3[F:36])[CH:18]=2)[NH:13][CH:12]=1)=[O:10]>CCO>[F:36][C:23]1[C:24]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])=[CH:25][CH:26]=[C:27]([F:28])[C:22]=1[C:21]([NH:20][C:17]1[CH:18]=[C:19]2[C:11]([C:9](=[O:10])[CH2:8][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:12][NH:13][C:14]2=[N:15][CH:16]=1)=[O:37]

Participants

Conditions

Temperature: 60 °C

Procedure

Piperidine (0.0105 mL, 0.106 mmol) was added to N-(3-(2-chloroacetyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.005 g, 0.0106 mmol) in EtOH (0.2 mL), which was stirred at 60° C. for 1 hour. The reaction mixture was cooled and concentrated under reduced pressure. The residue was purified via column chromatography (10% MeOH/EtOAc, to 30% MeOH (7N NH3/EtOAc). The pooled fractions were taken up in 10% MeOH/DCM and filtered to provide 2,6-difluoro-N-(3-(2-(piperidin-1-yl)acetyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (3 mg, 54.4%). 1H NMR (400 MHz, CD3OD) δ 9.05-9.07 (m, 1H), 8.54-8.57 (m, 1H), 8.44 (s, 1H), 7.63-7.69 (m, 1H), 7.12-7.17 (m, 1H), 4.71 (s, 2H), 3.59 (s, 2H), 3.10-3.14 (m, 2H), 1.92-1.99 (m, 6H), 1.84-1.90 (m, 2H), 1.04-1.08 (m, 3H); m/z (APCI-pos) M+1=520.2.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
customThe residue was purified via column chromatography (10% MeOH/EtOAc
filtrationfiltered

Sources & evidence

ORD record: ord-25b391c78f9d4c1b8b764d57b1487ad3
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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