Diisopropylethylamine → HCID 44223224, compound

HRID 2196653Notes

Reaction equation

CCN(C(C)C)C(C)C.[F:10][CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]1.Cl[CH2:18][C:19]([C:21]1[C:29]2[C:24](=[N:25][CH:26]=[C:27]([NH:30][C:31](=[O:47])[C:32]3[C:37]([F:38])=[CH:36][CH:35]=[C:34]([NH:39][S:40]([CH2:43][CH2:44][CH3:45])(=[O:42])=[O:41])[C:33]=3[F:46])[CH:28]=2)[NH:23][CH:22]=1)=[O:20]>CCO>[F:46][C:33]1[C:34]([NH:39][S:40]([CH2:43][CH2:44][CH3:45])(=[O:41])=[O:42])=[CH:35][CH:36]=[C:37]([F:38])[C:32]=1[C:31]([NH:30][C:27]1[CH:28]=[C:29]2[C:21]([C:19](=[O:20])[CH2:18][N:13]3[CH2:14][CH2:15][CH2:16][CH:11]([F:10])[CH2:12]3)=[CH:22][NH:23][C:24]2=[N:25][CH:26]=1)=[O:47]

Participants

Conditions

Temperature: 60 °C

Procedure

Hunig's base (0.0196 mL, 0.106 mmol) and 3-fluoropiperidine (0.0148 g, 0.106 mmol) were 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 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified via column chromatography (5% to 10% MeOH/DCM) to provide 2,6-difluoro-N-(3-(2-(3-fluoropiperidin-1-yl)acetyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (3 mg, 52.6%). 1H NMR (400 MHz, CD3OD) δ 8.90-8.92 (m, 1H), 8.62-8.63 (m, 1H), 8.60 (s, 1H), 7.63-7.69 (m, 1H), 7.13-7.16 (m, 1H), 4.60-4.80 (m, 1H), 3.76 (s, 2H), 3.08-3.15 (m, 2H), 2.86-2.94 (m, 1H), 2.59-2.79 (m, 4H), 2.50-2.55 (m, 1H), 1.80-1.93 (m, 4H), 1.57-1.71 (m, 2H), 1.04-1.08 (m, 3H); m/z (APCI-pos) M+1=538.1.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified via column chromatography (5% to 10% MeOH/DCM)

Sources & evidence

ORD record: ord-1bb89a16cce44e1a938fb8118afa69fe
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

Loading…