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

HRID 1508816노트

반응식

HRID 1508816 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
100 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-43d5eb96b9dc482b8ab43abc75aba80a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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