N,N-Dimethyl-1,3-propanediamine → 3'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide

HRID 719708Notes

Reaction equation

HRID 719708 reaction equation
[CH3:1][N:2]([CH3:32])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18](CSCCOC3C=CC=CC=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)=[O:8].[O:33]([CH2:40][CH2:41][S:42][CH2:43]C1C=C(C2C=CC=C(C(O)=O)C=2)C=CC=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CN(C)CCCN>C1COCC1>[CH3:32][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH2:43][S:42][CH2:41][CH2:40][O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:20]=2)[CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 103471824'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amideHCID 218999913'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid

Product 1

HCID 103249573'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide was synthesized as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide. 3′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (0.7 g, 1.92 mmol, 1 eq.) in anhydrous THF was treated with 1,1-carbonyldiimidazole (0.32 g, 1.96 mmol, 1.02 eq.), and 3-(dimethylamino)propylamine (0.30 g, 2.30 mmol, 1.2 eq.) as described. When complete, the reaction was worked up as described leaving a yellow oil.

Workup

  1. customas described leaving a yellow oil

Sources & evidence

ORD record
ord-64a11899ce16441fab996cf1766a535c
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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