Ammonia → 2-(4-((2-(3-Chlorophenyl)-6-(trifluoromethyl)pyridin-4-yl)amino)phenyl)acetamide

HRID 1508816ノート

反応式

HRID 1508816 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22](OCC)=[O:23])=[CH:17][CH:16]=3)[CH:11]=[C:10]([C:27]([F:30])([F:29])[F:28])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+:32].N>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([CH2:21][C:22]([NH2:32])=[O:23])=[CH:19][CH:20]=3)[CH:11]=[C:10]([C:27]([F:28])([F:30])[F:29])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 90112062Ethyl 2-(4-((2-(3-chlorophenyl)-6-(trifluoromethyl)pyridin-4-yl)amino)phenyl)acetate

生成物 1

HCID 901124342-(4-((2-(3-Chlorophenyl)-6-(trifluoromethyl)pyridin-4-yl)amino)phenyl)acetamide収率 46%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

A 10-mL vial was charged with ethyl 2-(4-((2-(3-chlorophenyl)-6-(trifluoromethyl)pyridin-4-yl)amino)phenyl)acetate (0.064 g, 0.15 mmol) and ammonium chloride (0.024 g, 0.44 mmol) in methanol (2 mL). To this mixture was added NH3 (4.2 mL, 7N in methanol, 29.4 mmol). The vial was sealed and the resulting mixture was stirred at 100° C. for 42 h. After this time, the crude reaction solution concentrated under reduced pressure. The residue absorbed on silica (2 g) then purified by chromatography on silica using dichloromethane/methanol (10:0 to 9:1) as eluent to afford the title compound (0.027 g, 46%) as a light brown solid. MW=405.80. M.p. 97-99° C. 1H NMR (DMSO-d6, 500 MHz) δ 9.39 (s, 1H), 7.99-7.97 (m, 1H), 7.91-7.86 (m, 1H), 7.57-7.51 (m, 3H), 7.46 (br s, 1H), 7.33-7.29 (m, 2H), 7.27-7.23 (m, 2H), 7.19 (d, J=2.0 Hz, 1H), 6.88 (br s, 1H), 3.37 (s, 2H); APCI MS m/z 406 [M+H]+.

後処理

  1. customThe vial was sealed
  2. customAfter this time, the crude reaction solution
  3. concentrationconcentrated under reduced pressure
  4. customThe residue absorbed on silica (2 g)
  5. customthen purified by chromatography on silica

出典と根拠

ORDレコード
ord-43d5eb96b9dc482b8ab43abc75aba80a
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

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