N,N-Dimethylethylenediamine → 3'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amide

HRID 719713Notes

Reaction equation

HRID 719713 reaction equation
[O:1]([CH2:8][CH2:9][S:10][CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24](O)=[O:25])=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH2:31]>C1COCC1>[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH:31][C:24]([C:21]1[CH:22]=[CH:23][C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][S:10][CH2:9][CH2:8][O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:13]=2)=[CH:19][CH:20]=1)=[O:25]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 218999793'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid

Product 1

HCID 98891473'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amide was synthesized as described for 41-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide. 3′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (0.80 g, 2.19 mmol, 1 eq.) in anhydrous THF was treated with 1,1-carbonyldiimidazole (0.36 g, 2.23 mmol, 1.02 eq.) and N,N-dimethylethylenediamine (0.23 g, 2.63 mmol, 1.2 eq.). When complete, the reaction was worked up as described leaving a yellow oil that later solidified.

Workup

  1. customas described leaving a yellow oil

Sources & evidence

ORD record
ord-1cdaf8522c2248b99a2bc14481d3d6e9
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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