Dimethylamine → HCID 44223171, compound

HRID 2196649Notes

Reaction equation

Cl[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([NH:14][C:15](=[O:31])[C:16]3[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]=3[F:30])[CH:12]=2)[NH:7][CH:6]=1)=[O:4].[CH3:32][NH:33][CH3:34].CO>CCO>[CH3:32][N:33]([CH3:34])[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([NH:14][C:15](=[O:31])[C:16]3[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]=3[F:30])[CH:12]=2)[NH:7][CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

N-(3-(2-Chloroacetyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.181 mL, 0.0361 mmol), EtOH (0.2 mL), and dimethylamine as a solution in MeOH (0.181 mL, 0.361 mmol) was charged to a 2 dram vial. The vial was capped and stirred at 60° C. for 4 hours. The mixture was concentrated under reduced pressure. The residue was taken up in 1M HCL (1 mL) and washed with EtOAc (2×1 mL). The aqueous portion was neutralized and extracted with 25% isopropyl alcohol (“IPA”)-DCM (3×2 mL), which was concentrated to provide N-(3-(2-(dimethylamino)acetyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (7 mg, 40.4%) as a solid. 1H NMR (400 MHz, CD3OD) δ 9.03-9.06 (m, 1H), 8.56-8.58 (m, 1H), 8.46 (s, 1H), 7.63-7.69 (m, 1H), 7.12-7.16 (m, 1H), 3.11-3.14 (m, 2H), 3.03 (s, 6H), 2.90 (s, 2H), 1.85-1.90 (m, 2H), 1.05-1.08 (m, 3H); m/z (APCI-pos) M+1=480.1.

Workup

customThe vial was capped
concentrationThe mixture was concentrated under reduced pressure
washwashed with EtOAc (2×1 mL)
extractionextracted with 25% isopropyl alcohol (“IPA”)-DCM (3×2 mL), which
concentrationwas concentrated

Sources & evidence

ORD record: ord-05b89bc28a4f4481ba1b7d324aad60f0
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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