Sodium Hydroxide → 3-Bromo-6-chloro-4-[methyl(oxan-4-yl)amino]pyridine-2-carboxylic acid
반응식
[Br:1][C:2]1[C:3]([C:17]([O:19]C)=[O:18])=[N:4][C:5]([Cl:16])=[CH:6][C:7]=1[N:8]([CH3:15])[CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[C:3]([C:17]([OH:19])=[O:18])=[N:4][C:5]([Cl:16])=[CH:6][C:7]=1[N:8]([CH3:15])[CH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1참가 물질
실험 절차
To a stirred solution of methyl 3-bromo-6-chloro-4-[methyl(oxan-4-yl)amino]pyridine-2-carboxylate (102 mg, 0.28 mmol) in THF (2 ml) was added 2M aqueous NaOH (0.70 ml, 1.40 mmol) and the reaction mixture was left to stir at room temperature for 18 h after which time the THF was evaporated in vacuo. The aqueous phase was then treated with an aqueous 10% citric acid solution to 5-6 and then extracted with EtOAc (3×50 ml) followed by a solution of 1:1 IPA/CHCl3 (2×50 ml), the combined organic phases were then washed with brine (50 ml) dried with Na2SO4 and evaporated to give the title compound as a white solid (72 mg, 73%). LC-MS 100%, 1.49 min (3.5 minute LC-MS method), m/z=349.0/351.0/352.9, 1H NMR (500 MHz, Methanol-d4) δ 7.07 (s, 1H), 4.02 (dd, J=11.3, 4.3 Hz, 2H), 3.96-3.87 (m, 1H), 3.46 (t, J=11.0 Hz, 2H), 2.85 (s, 3H), 1.96 (dd, J=12.3, 4.3 Hz, 2H), 1.77 (s, 2H).
후처리
- waitthe reaction mixture was left
- customwas evaporated in vacuo
- additionThe aqueous phase was then treated with an aqueous 10% citric acid solution to 5-6
- extractionextracted with EtOAc (3×50 ml)
- washthe combined organic phases were then washed with brine (50 ml)
- dry with materialdried with Na2SO4
- customevaporated
출처 및 근거
- ORD 기록
- ord-8c3f9a38355342198295bae36a72e689
- 출처 데이터셋
- uspto-grants-2016_06
- 특허 번호
- US09376422B2
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