Acetyl chloride → HCID 66926924, 화합물

HRID 81066노트

반응식

HRID 81066 반응식
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:19]=[C:18]([Cl:20])[C:15]([C:16]#[N:17])=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:23][CH:22]=3)[N:13]=2)=[CH:8][CH:7]=1.CCN(C(C)C)C(C)C>ClCCl>[Cl:20][C:18]1[C:15]([C:16]#[N:17])=[C:14]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:23][CH:22]=2)[N:13]=[C:12]([C:9]2[CH:8]=[CH:7][C:6]([NH:5][C:1](=[O:3])[CH3:2])=[CH:11][CH:10]=2)[CH:19]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chloride2회HCID 81531DiisopropylethylamineHCID 669269446-(4-Aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile

생성물 1

HCID 66926924HCID 66926924, 화합물수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Acetyl chloride (0.013 mL, 0.181 mmol) was added to a suspension of 6-(4-aminophenyl)-4-chloro-2-(4-phenoxyphenyl)nicotinonitrile (48 mg, 0.121 mmol, from Step 3 of Example 199) and Hunig's base (0.084 mL, 0.483 mmol) in dichloromethane (1 mL) at room temperature. After 90 min at room temperature, additional acetyl chloride (0.05 mL) was added. After additional 23 h, the reaction was stopped and the mixture purified by silica gel chromatography, eluting with 0-60% ethyl acetate in hexanes, to give N-(4-(4-chloro-5-cyano-6-(4-phenoxyphenyl)pyridin-2-yl)phenyl)acetamide as yellow solid (24.9 mg, 47% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.11 (2H, δ, J=8.78 Hz), 8.00-8.03 (2H, m), 7.79 (1H, s), 7.68 (2H, δ, J=8.53 Hz), 7.35-7.44 (3H, m), 7.19 (1H, t, J=7.40 Hz), 7.08-7.15 (4H, m), 2.23 (3H, s); MS (ES+) m/z: 440 (M+H); LC retention time: 4.668 min (analytical HPLC Method A). Unreacted starting material was also recovered (13.7 mg).

후처리

  1. waitAfter additional 23 h
  2. customthe mixture purified by silica gel chromatography
  3. washeluting with 0-60% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-ba4295629efc40678e010190f2af391d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846673B2

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