Ammonia methanol dichloromethane → 3-(4'-Chlorobiphenyl-4-yl)propynoic acid-(4-{[(2-methoxyethyl)methylamino]methyl}phenyl)amide

HRID 735046Notes

Reaction equation

HRID 735046 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]([OH:18])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:19][O:20][CH2:21][CH2:22][N:23]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)[CH3:24].ClCCl.CO.N>>[CH3:19][O:20][CH2:21][CH2:22][N:23]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:16](=[O:18])[C:15]#[C:14][C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:13][CH:12]=2)=[CH:30][CH:31]=1)[CH3:24]

Participants

4

Reactant 3

HCID 21584172Ammonia methanol dichloromethaneHCID 235074614-{[(2-Methoxyethyl)methylamino]methyl}phenylamineHCID 68816492(4'-Chlorobiphenyl-4-yl)propynoic acid

Product 1

HCID 578458493-(4'-Chlorobiphenyl-4-yl)propynoic acid-(4-{[(2-methoxyethyl)methylamino]methyl}phenyl)amide

Procedure

Prepared analogously to Example 3.8. from (4′-chlorobiphenyl-4-yl)propynoic acid and 4-{[(2-methoxyethyl)methylamino]methyl}phenylamine. Yield: 150 mg (35% of theory); melting point: 130° C.-133° C.; C26H25ClN2O2 (M=432.94); calc.: molecular ion peak (M+H)+: 433/435 (Cl); found: molecular ion peak (M+H)+: 433/435 (Cl); Rf value: 0.50 (silica gel, dichloromethane/methanol/ammonia (90:10:1)).

Workup

  1. customPrepared analogously to Example 3.8

Sources & evidence

ORD record
ord-56570c018f9c44539a62c10518429cf7
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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