1,1'-Carbonyldiimidazole → 4'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (4-dimethylamino-butyl)-amide

HRID 719696Notes

Reaction equation

HRID 719696 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]([CH3:46])[CH2:41][CH2:42][CH2:43][CH2:44][NH2:45]>C1COCC1>[CH3:39][N:40]([CH3:46])[CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:24]([C:19]1[C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][S:10][CH2:9][CH2:8][O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:17][CH:16]=2)=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:26]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 770634-DimethylaminobutylamineHCID 218999824'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid

Product 1

HCID 103253264'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (4-dimethylamino-butyl)-amideYield 98.3%

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 (0.85 g, 2.33 mmol, 1 eq.) in anhydrous THF was treated with 1,1′-carbonyldiimidazole (0.40 g, 2.45 mmol, 1.05 eq.) and warmed as described. The reaction was allowed to cool and then treated with 4-dimethylaminobutylamine (0.33 g, 2.80 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 5% 2M NH3 in methanol in chloroform 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 (4-dimethylamino-butyl)-amide (1.06 g, 98% 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-a01c7780bb4a49fe9b532b6485c1a380
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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