1,1'-Carbonyldiimidazole → 4'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (4-dimethylamino-butyl)-amide

HRID 719688Notes

Reaction equation

HRID 719688 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]([OH:26])=O)=[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(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:39][N:40]([CH3:46])[CH2:41][CH2:42][CH2:43][CH2:44][NH2:45]>C1COCC1>[CH3:39][N:40]([CH3:46])[CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:24]([C:21]1[CH:22]=[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]=1)=[O:26]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 770634-DimethylaminobutylamineHCID 218999774'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid

Product 1

HCID 99850894'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (4-dimethylamino-butyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (4-dimethylamino-butyl)-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 4-dimethylaminobutylamine (0.28 g, 2.41 mmol, 1.1 eq.). When complete, the reaction was worked up to leave a yellow oil (0.72 g, 71% yield) which solidified on standing. The free base was converted to the oxalate as described in example 3 to give 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (4-dimethylamino-butyl)-amide oxalate (0.61 g) as a white solid.

Sources & evidence

ORD record
ord-57010c7928b94cb482187fe404cf4470
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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