Ethyl Acetate → 5-Amino-1-(1-naphthyl)-3-(4-tolyl)pyrazole-4-carboxamide

HRID 582011

반응식

HRID 582011 반응식
[C:1]([C:3](=[C:7](SC)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[C:18]1([NH:28][NH2:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].C(OCC)(=O)C>CCCCCC>[NH2:2][C:1]1[N:28]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[N:29]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 519949Hydrazine, 1-naphthalenyl-, hydrochloride (1:1)HCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2회

생성물 1

HCID 543553485-Amino-1-(1-naphthyl)-3-(4-tolyl)pyrazole-4-carboxamide수율 27%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl) acrylamide (464 mg, 2.0 mmol), 1-naphthyl hydrazine hydrochloride (389 mg, 2.0 mmol) and sodium hydroxide (88 mg, 2.2 mmol) following the procedure used for the compound of Example 12. The crude product was subjected to column chromatography (SiO2, 50-60% ethyl acetate in hexane) and was recrystallised from diethylether to give the title compound as pink crystals (185 mg) m.p. 195°. δH (CDCl3) 8.00 (1H, d, J 8.3 Hz), 7.95 (1 H., m), 7.73-7.55 (7H, m), 7.30 (2H, d, J 8.3 Hz), 5.52 (2H, br s), 5.16 (2H, br s) and 2.42 (3H, s).

후처리

  1. customwas recrystallised from diethylether

출처 및 근거

ORD 기록
ord-ef930def809749ab9ca3e9e30e78bcdb
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922741

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