Sodium Hydroxide → 3-Bromo-6-chloro-4-[methyl(oxan-4-yl)amino]pyridine-2-carboxylic acid

HRID 2208806ノート

反応式

HRID 2208806 の反応式
[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]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 86719561Methyl 3-bromo-6-chloro-4-[methyl(oxan-4-yl)amino]pyridine-2-carboxylate

生成物 1

HCID 867195623-Bromo-6-chloro-4-[methyl(oxan-4-yl)amino]pyridine-2-carboxylic acid収率 73.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  1. waitthe reaction mixture was left
  2. customwas evaporated in vacuo
  3. additionThe aqueous phase was then treated with an aqueous 10% citric acid solution to 5-6
  4. extractionextracted with EtOAc (3×50 ml)
  5. washthe combined organic phases were then washed with brine (50 ml)
  6. dry with materialdried with Na2SO4
  7. customevaporated

出典と根拠

ORDレコード
ord-8c3f9a38355342198295bae36a72e689
出典データセット
uspto-grants-2016_06
特許番号
US09376422B2

反応ノート

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