4-chloro-6-hydrazinyl-2-(4-phenoxyphenyl)-5-phenylnicotinonitrile TFA salt → HCID 86665693, 화합물

HRID 81055노트

반응식

HRID 81055 반응식
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[Cl:8][C:9]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[N:12]=[C:11](NN)[C:10]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>S([O-])([O-])(=O)=O.[Cu+2].C(O)CC>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[Cl:8][C:9]1[C:14]([C:15]#[N:16])=[C:13]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:22]=2)[N:12]=[CH:11][C:10]=1[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

참가 물질

4

반응물 1

HCID 866656944-chloro-6-hydrazinyl-2-(4-phenoxyphenyl)-5-phenylnicotinonitrile TFA salt

생성물 1

HCID 86665693HCID 86665693, 화합물수율 26.1%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 10311-Propanol용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-chloro-6-hydrazinyl-2-(4-phenoxyphenyl)-5-phenylnicotinonitrile TFA salt (72.6 mg, 0.138 mmol), 1.0 M aqueous copper(II) sulfate (0.276 mL, 0.276 mmol) and 1-propanol (1 mL) was heated to 100° C. in a sealed tube for 2 h. After cooling to room temperature, the mixture was filtered. The filtrate was concentrated and purified by reverse phase HPLC (isocratic 100% solvent B for 25 min, 40 mL/min, Sunfire 30×250 mm to give 4-chloro-2-(4-phenoxyphenyl)-5-phenylnicotinonitrile TFA salt as white solid (17.9 mg, 26% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.78 (1H, s), 7.87-7.96 (2H, m), 7.46-7.56 (5H, m), 7.37-7.45 (2H, m), 7.20 (1H, t, J=7.40 Hz), 7.09-7.17 (4H, m); MS (ES+) m/z: 383 (M+H); LC retention time: 4.790 min (analytical HPLC Method A).

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated
  4. custompurified by reverse phase HPLC (isocratic 100% solvent B for 25 min

출처 및 근거

ORD 기록
ord-4ded2ca8572d485e80e7e18ffcd8359f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846673B2

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