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

HRID 719722Notes

Reaction equation

HRID 719722 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:49]=[CH:48][CH:47]=[CH:46][C:45]=1[C:50]1[C:51]([C:56]([OH:58])=O)=[CH:52][CH:53]=[CH:54][CH:55]=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:51]1[C:50]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[CH2:43][S:42][CH2:41][CH2:40][O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:58]

Participants

5

Reactant 3

HCID 770634-DimethylaminobutylamineHCID 103471824'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amideHCID 218999762'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid

Product 1

HCID 100991302'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (4-dimethylamino-butyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (4-dimethylamino-butyl)-amide was synthesized as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide. 2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (1.0 g, 2.74 mmol, 1 eq.) in anhydrous THF was treated with 1,1-carbonyldiimidazole (0.45 g, 2.79 mmol, 1.02 eq.) and 4-dimethylaminobutylamine (0.35 g, 3.01 mmol, 1.1 eq.). When complete, the reaction was worked up as described leaving a brown oil.

Workup

  1. customas described leaving a brown oil

Sources & evidence

ORD record
ord-0bfa229e76714b2fab2e9d2994d49889
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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