4-Amino-4'-methoxybiphenyl → (E)-N-(4'-methoxybiphenyl-4-yl)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylamide

HRID 735166Notes

Reaction equation

HRID 735166 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.ClCCl.CO.N>>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:15](=[O:17])/[CH:14]=[CH:13]/[C:10]3[CH:9]=[CH:8][C:7]([CH2:6][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)=[CH:12][CH:11]=3)=[CH:28][CH:27]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 27595644-Amino-4'-methoxybiphenylHCID 21584172Ammonia methanol dichloromethaneHCID 68815843(E)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylic Acid

Product 1

HCID 57845721(E)-N-(4'-methoxybiphenyl-4-yl)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylamide

Procedure

Prepared analogously to Example 3.1.e. from (E)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylic acid and 4′-methoxybiphenyl-4-ylamine. Yield: 74 mg (15.4% of theory); melting point: 199° C.-200° C.; C27H28N2O2 (M=412.53); calc.: molecular ion peak (M+H)+: 413; found: molecular ion peak (M+H)+: 413; Rf value: 0.77 (silica gel, dichloromethane/methanol/ammonia (80:20:1)).

Workup

  1. customPrepared analogously to Example 3.1.e

Sources & evidence

ORD record
ord-ae53f41e392c44fcbd89ccdc30883030
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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