Hydrochloric Acid → 6-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxylic acid

HRID 1714864ノート

反応式

HRID 1714864 の反応式
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[N:16][C:15]([C:18]([O:20]C)=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.O.[OH-].[Li+].Cl>C1COCC1.O>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[N:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68505610Methyl 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxylate

生成物 1

HCID 462254266-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of methyl 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxylate (800 mg, 2.1 mmol) and lithium hydroxide monohydrate (352 mg, 8.4 mmol) in THF (10 mL) and water (5 mL) was stirred at r.t. overnight, then acidified with 1M aqueous HCl (9 mL). Volatile materials were removed in vacuo. The residue was diluted with water and extracted with EtOAc. The organic extract was washed with diluted brine, dried (Na2SO4), concentrated and swished with Et2O to give the title compound as a white powder. 1H NMR (400 MHz, acetone-d6): δ 1.97 (m, 2H), 2.15-2.21 (m, 2H), 4.00-4.10 (m, 4H), 5.04-5.08 (m, 1H), 7.13 (t, 1H), 7.39 (m, 2H), 7.63-7.69 (m, 2H), 7.94 (d, 1H).

後処理

  1. customVolatile materials were removed in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with diluted brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-a0181077ca404f4f8125e1c489677742
出典データセット
uspto-grants-2010_09
特許番号
US07799787B2

反応ノート

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