2-(Trifluoromethoxy)benzoyl Chloride → 2-Trifluoromethoxy-N-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide mono-hydrochloride salt

HRID 30210ノート

反応式

HRID 30210 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[N:3]=1.[F:17][C:18]([F:30])([F:29])[O:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([Cl:24])=[O:23]>O1CCOCC1>[ClH:24].[F:17][C:18]([F:29])([F:30])[O:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[N:3]=1)=[O:23]

参加物

4

反応物 2

HCID 27772412-(Trifluoromethoxy)benzoyl ChlorideHCID 11401723(6-Aminopyridin-2-yl)(1-methylpiperidin-4-yl)methanone

生成物 1

HCID 179803882-Trifluoromethoxy-N-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide mono-hydrochloride salt収率 76%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

Combine 2-amino-6-(1-methylpiperidin-4-ylcarbonyl)pyridine (0.18 g, 0.84 mmol), 2-trifluoromethoxybenzoyl chloride (0.23 g, 1.0 mmol) and 1,4-Dioxane (5 mL). Stir and heat the mixture at reflux. After 3 hr., cool the reaction mixture to ambient temperature. Load on an SCX column (10 g), wash with methanol, and elute with 2M ammonia/methanol. Concentrate the eluent to obtain the free base of the title compound (0.26 g, 76%). Dissolve the free base in methanol (10 mL) and treat with ammonium chloride (0.032 g). Concentrate and dry under vacuum to obtain the title compound. HRMS Obs. m/z 408.1517, Calc. m/z 408.1535; m.p. 155-160° C.

後処理

  1. temperatureheat the mixture
  2. temperatureat reflux
  3. washLoad on an SCX column (10 g), wash with methanol
  4. washelute with 2M ammonia/methanol
  5. concentrationConcentrate the eluent

出典と根拠

ORDレコード
ord-ac0f35488146473ea80a7be32996d9f7
出典データセット
uspto-grants-2008_09
特許番号
US07423050B2

反応ノート

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