Hydrochloric Acid → 5-Chloro-2-methyl-3-((1-(pyrimidin-4-yl)piperidin-4-yl)oxy)benzoic acid
反応式
[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][N:21]=3)[CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][N:21]=3)[CH2:18][CH2:19]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]参加物
実験手順
To a solution of methyl 5-chloro-2-methyl-3-((1-(pyrimidin-4-yl)piperidin-4-yl)oxy)benzoate (335 mg, 0.926 mmol) in methanol (10 mL) was added 8 M sodium hydroxide (0.926 mL, 7.41 mmol). The resulting solution was stirred at room temperature for 3 days, at which time the methanol was removed in vacuo and the residue diluted with water (2 mL). The mixture was acidified with 6 M HCl (1.157 mL, 6.94 mmol) and the resulting suspension was stirred at room temperature for 20 min. The white solid was collected via vacuum filtration and air dried under vacuum to give 5-chloro-2-methyl-3-((1-(pyrimidin-4-yl)piperidin-4-yl)oxy)benzoic acid (172 mg, 0.494 mmol, 53.4% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.22 (br. s., 1H), 8.50 (s, 1H), 8.18 (d, J=6.32 Hz, 1H), 7.35 (d, J=2.02 Hz, 1H), 7.29 (d, J=2.02 Hz, 1H), 6.88 (dd, J=1.26, 6.32 Hz, 1H), 4.82 (tt, J=3.60, 7.26 Hz, 1H), 3.91 (d, J=4.55 Hz, 2H), 3.51-3.72 (m, 2H), 2.30 (s, 3H), 1.89-2.04 (m, 2H), 1.54-1.74 (m, 2H). MS(ES) [M+H]+ 348.1.
後処理
- customwas removed in vacuo
- additionthe residue diluted with water (2 mL)
- filtrationThe white solid was collected via vacuum filtration and air
- customdried under vacuum
出典と根拠
- ORDレコード
- ord-44fd69d56f034c4aa14178457dbb2b65
- 出典データセット
- uspto-grants-2016_07
- 特許番号
- US09382234B2
反応ノート
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