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

HRID 719734Notes

Reaction equation

HRID 719734 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[CH:55]=[CH:54][C:53]([C:56]([OH:58])=O)=[CH:52][CH:51]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[CH3:59][N:60]([CH3:64])[CH2:61][CH2:62][NH2:63]>C1COCC1>[CH3:59][N:60]([CH3:64])[CH2:61][CH2:62][NH:63][C:56]([C:53]1[CH:52]=[CH:51][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]=1)=[O:58]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 103471824'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amideHCID 218999832'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid

Product 1

HCID 104780742'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amide was synthesized as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide. 2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (0.80 g, 2.19 mmol, 1 eq.) in anhydrous THF was treated with 1,1-carbonyldiimidazole (0.36 g, 2.23 mmol, 1.02 eq.) followed by N,N-dimethylethylenediamine (0.23 g, 2.63 mmol, 1.2 eq.) as described. When complete, the reaction was worked up leaving a yellow oil. The oil was purified via silica gel flash chromatography using 140:10:1 (CHCl3/MeOH/NH4OH) as the mobile phase. Fractions containing the product were pooled and the solvent removed in vacuo leaving 2′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amide (0.95 g, 100% yield) as a yellow oil. Recrystallized from diethyl ether to obtain 2′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amide (0.49 g) as a white solid that was collected by filtration.

Workup

  1. custom2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-amide was synthesized
  2. customWhen complete, the reaction was worked up leaving a yellow oil
  3. customThe oil was purified via silica gel flash chromatography
  4. additionFractions containing the product
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2d89bcbc1ab241c8a066b4a256cc2105
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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