4-Dimethylaminobutylamine → 3'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (4-dimethylamino-butyl)-amide

HRID 719715Notes

Reaction equation

HRID 719715 reaction equation
CN(C)CCCNC(C1C=C(C2C=CC(CSCCOC3C=CC=CC=3)=CC=2)C=CC=1)=O.[O:33]([CH2:40][CH2:41][S:42][CH2:43][C:44]1[CH:45]=[C:46]([C:50]2[CH:55]=[CH:54][C:53]([C:56]([OH:58])=O)=[CH:52][CH:51]=2)[CH:47]=[CH:48][CH:49]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[CH3:59][N:60]([CH3:66])[CH2:61][CH2:62][CH2:63][CH2:64][NH2:65]>C1COCC1>[CH3:59][N:60]([CH3:66])[CH2:61][CH2:62][CH2:63][CH2:64][NH:65][C:56]([C:53]1[CH:54]=[CH:55][C:50]([C:46]2[CH:47]=[CH:48][CH:49]=[C:44]([CH2:43][S:42][CH2:41][CH2:40][O:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:45]=2)=[CH:51][CH:52]=1)=[O:58]

Participants

5

Reactant 3

HCID 770634-DimethylaminobutylamineHCID 103471824'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amideHCID 218999793'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid

Product 1

HCID 104827433'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (4-dimethylamino-butyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (4-dimethylamino-butyl)-amide was synthesized as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide. 3′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (1.50 g, 4.12 mmol, 1 eq.) in anhydrous THF was treated with 1,1-carbonyldiimidazole (0.68 g, 4.20 mmol, 1.02 eq.) and 4-dimethylaminobutylamine (0.57 g, 4.94 mmol, 1.2 eq.). 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-fa4c5514457b4629817b57e1f08fad89
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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