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

HRID 719728Notes

Reaction equation

HRID 719728 reaction equation
[CH3:1][N:2]([CH3:32])[CH2:3][CH2:4][CH2:5][NH:6]C(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][CH:53]=[C:52]([C:56](O)=[O:57])[CH:51]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CN(C)CCCN>C1COCC1>[CH3:1][N:2]([CH3:32])[CH2:3][CH2:4][CH2:5][NH:6][C:56]([C:52]1[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:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:55]=[CH:54][CH:53]=1)=[O:57]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 103471824'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amideHCID 218999962'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid

Product 1

HCID 104372642'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2′-(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. 2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-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.) followed by 3-(dimethylamino)propylamine (0.34 g, 3.29 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 10% 2M NH3 in methanol in chloroform as the mobile phase. Fractions containing the product were pooled and the solvent removed in vacuo leaving 2′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide (1.06 g, 86% yield). The free base was converted to the oxalate salt by adding oxalic acid (0.26 g, 1.2 eq.) in EtOAc dropwise to an EtOAc solution of the free base. 2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide oxalate (1.08 g) was collected by filtration as a white solid.

Workup

  1. custom2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-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-da6314f2bf0b494dae511de6db562640
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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