Triethylamine → (E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-{[methyl-(4-methylcyclohexyl)amino]methyl}phenyl)acrylamide

HRID 735176

반응식

HRID 735176 반응식
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15](=[O:30])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)(=O)=O.[CH3:31][NH:32][CH:33]1[CH2:38][CH2:37][CH:36]([CH3:39])[CH2:35][CH2:34]1.C(N(CC)CC)C>ClCCl>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([C:20]2[CH:19]=[CH:18][C:17]([NH:16][C:15](=[O:30])/[CH:14]=[CH:13]/[C:10]3[CH:11]=[CH:12][C:7]([CH2:6][N:32]([CH3:31])[CH:33]4[CH2:38][CH2:37][CH:36]([CH3:39])[CH2:35][CH2:34]4)=[CH:8][CH:9]=3)=[CH:22][CH:21]=2)=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 4962029N,4-DimethylcyclohexanamineHCID 866018934-[(E)-2-(4'-chlorobiphenyl-4-ylcarbamoyl)vinyl]benzyl Methanesulfonate

생성물 1

HCID 57845832(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-{[methyl-(4-methylcyclohexyl)amino]methyl}phenyl)acrylamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A reaction mixture of 100 mg (0.226 mmol) of 4-[(E)-2-(4′-chlorobiphenyl-4-ylcarbamoyl)vinyl]benzyl methanesulfonate, 37.34 mg (0.29 mmol) of methyl-(4-methylcyclohexyl)amine, and 0.1 mL of triethylamine in 10 mL of dichloromethane is stirred for 18 hours at ambient temperature. Then the reaction mixture is extracted between water and dichloromethane, the organic phase is separated off, dried, and evaporated down. The residue is purified by column chromatography on silica gel (eluant: dichloromethane/methanol/ammonia (90:10:1)). Yield: 52 mg (49% of theory); C30H33ClN2O (M=473.05); melting point: 227° C.-258° C.; calc.: molecular ion peak (M+H)+: 473/475 (Cl); found: molecular ion peak (M+H)+: 473/475 (Cl); Rf value: 0.48 (silica gel, dichloromethane/methanol/ammonia (90:10:1)).

후처리

  1. extractionThen the reaction mixture is extracted between water and dichloromethane
  2. customthe organic phase is separated off
  3. customdried
  4. customevaporated down
  5. customThe residue is purified by column chromatography on silica gel (eluant: dichloromethane/methanol/ammonia (90:10:1))

출처 및 근거

ORD 기록
ord-578f5fe04aba4cb2a44fce535e45c905
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592373B2

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