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Methanol → 5-Amino-1-[(ethoxycarbonyl)methyl]-3-(4-tolyl)pyrazole-4-carboxamide

HRID 582009
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HRID 582009 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.[NH:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[NH2:19].[OH-].[Na+].CO>C(Cl)Cl>[NH2:2][C:1]1[N:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:19]=[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]
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참가 물질

6

반응물 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)HCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2회

생성물 1

HCID 540028605-Amino-1-[(ethoxycarbonyl)methyl]-3-(4-tolyl)pyrazole-4-carboxamide수율 27.5%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl)acrylamide (425 mg, 1.83 mmol), ethyl hydrazinoacetate hydrochloride (311 mg, 2.01 mmol) and sodium hydroxide (80 mg, 2.01 mmol) following the procedure used for the compound of Example 12. The crude product was subjected to column chromatography (SiO2, 10% methanol in CH2Cl2) and was recrystallised from ethyl acetate to give the title compound as white crystals (152 mg) m.p. 179°. δH (CDCl3) 7.43 (2H, d, J 8.1 Hz), 7.26 (2H, d, J 8.1 Hz), 5.56 (2H, br s), 5.22 (2H, br s), 4.77 (2H, s), 4.27 (2H, q, J 7.2 Hz), 2.40 (3H, s) and 1.32 (3H, t, J 7.2 Hz).

후처리

  1. customwas recrystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-ee0b6ada0b1645d7bc9014a9ca733bef
출처 데이터셋
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05922741

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