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

HRID 719680Notes

Reaction equation

HRID 719680 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][CH:21]=[C:20](C(O)=O)[CH:19]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([N:34]1[CH:38]=[CH:37][N:36]=[CH:35]1)(N1C=CN=C1)=[O:28].[CH3:39]NCCNC>>[CH3:39][N:36]([CH3:35])[CH2:37][CH2:38][NH:34][C:27]([C:22]1[CH:23]=[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:19]=[CH:20][CH:21]=1)=[O:28]

Participants

4

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 218999924'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid

Product 1

HCID 100297774'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(2-dimethylamino-ethyl)-amideYield 94%

Procedure

Prepared in the same manner as described for example 1. A solution of 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(0.68 g, 1.87 mmol, 1 eq.) was treated with 1,1′-carbonyldiimidazole (0.31 g, 1.91 mmol, 1.02 eq.) and warmed as described. The reaction was allowed to cool and then treated with N′,N-dimethylethylenediamine (0.20 g, 2.24 mmol, 1.2 eq.). The reaction was treated as described in example 1 to give 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(2-dimethylamino-ethyl)-amide (0.76 g, 94% yield) as a faint yellow oil.

Workup

  1. customPrepared in the same manner
  2. temperaturewarmed
  3. temperatureto cool
  4. additionThe reaction was treated

Sources & evidence

ORD record
ord-739f519caed545349b042b959e095a2b
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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