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

HRID 719686Notes

Reaction equation

HRID 719686 reaction equation
[O:1]([CH2:8][CH2:9][S:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24](O)=[O:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](N1C=CN=C1)([N:29]1[CH:33]=[CH:32][N:31]=[CH:30]1)=O.CN(C)CCN>C1COCC1>[CH3:27][N:29]([CH3:30])[CH2:33][CH2:32][NH:31][C:24]([C:21]1[CH:20]=[CH:19][C:18]([C:15]2[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][CH:14]=2)=[CH:23][CH:22]=1)=[O:25]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 218999774'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid

Product 1

HCID 103920804'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amideYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amide was prepared as described in example 1. 4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (0.8 g, 2.19 mmol, 1 eq.) in THF was treated with 1,1′-carbonyldiimidazole (0.36 g, 2.23 mmol, 1.02 eq.). The resulting acyl imidazole was then treated with N,N-dimethylethylenediamine (0.23 g, 2.63 mmol, 1.2 eq). When complete, the reaction was worked up and the resulting yellow oil purified as described in example 3 to give 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amide (0.82 g, 86% yield) as a yellow oil.

Workup

  1. custom4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amide was prepared
  2. customthe resulting yellow oil purified

Sources & evidence

ORD record
ord-d45435250c0c470ca399df9b58fed366
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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