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

HRID 735176

Reaction equation

HRID 735176 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)).

Workup

  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))

Sources & evidence

ORD record
ord-578f5fe04aba4cb2a44fce535e45c905
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Linked notes

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