N,N-Dimethyl-1,3-propanediamine → 4'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (3-dimethylamino-propyl)-amide

HRID 719695Notes

Reaction equation

HRID 719695 reaction equation
[O:1]([CH2:8][CH2:9][S:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]([OH:26])=O)=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:39][N:40]([CH3:45])[CH2:41][CH2:42][CH2:43][NH2:44]>C1COCC1>[CH3:39][N:40]([CH3:45])[CH2:41][CH2:42][CH2:43][NH:44][C:24]([C:19]1[C:18]([C:15]2[CH:16]=[CH:17][C:12]([CH2:11][S:10][CH2:9][CH2:8][O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:13][CH:14]=2)=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:26]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 682631,1'-CarbonyldiimidazoleHCID 218999824'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid

Product 1

HCID 99811164'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (3-dimethylamino-propyl)-amideYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared in the same manner as described for example 1. A solution of 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (0.38 g, 1.04 mmol, 1 eq.) in anhydrous THF was treated with 1,1′-carbonyldiimidazole (0.17 g, 1.06 mmol, 1.02 eq.) and warmed as described. The reaction was allowed to cool and then treated with 3-(dimethylamino)propylamine (0.13 g, 1.25 mmol, 1.2 eq.). The reaction was treated as described in example 1 to give a yellow oil. The oil was purified by silica gel flash chromatography using 10% 2M NH3 in methanol in diethyl ether as the mobile phase. Fractions containing the product were pooled and the solvent removed in vacuo leaving 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (3-dimethylamino-propyl)-amide (0.40 g, 85% yield) as a light yellow oil.

Workup

  1. customPrepared in the same manner
  2. temperaturewarmed
  3. temperatureto cool
  4. additionThe reaction was treated
  5. customto give a yellow oil
  6. customThe oil was purified by silica gel flash chromatography
  7. additionFractions containing the product
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6f0870eead644d15bee59f0470cb3272
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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