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

HRID 719720Notes

Reaction equation

HRID 719720 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](O)=[O:57])=[CH:52][CH:53]=[CH:54][CH:55]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[C:59](N1C=CN=C1)([N:61]1[CH:65]=[CH:64][N:63]=[CH:62]1)=O.CN(C)CCN>C1COCC1>[CH3:59][N:61]([CH3:62])[CH2:65][CH2:64][NH:63][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:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:57]

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 103471824'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amideHCID 218999762'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid

Product 1

HCID 104594742'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl 2-carboxylic acid (2-dimethylamino-ethyl)-amideYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-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-2-carboxylic acid (0.8 g, 2.19 mmol, 1 eq.) in anhydrous THF was treated with 1,1′-carbonyldiimidazole (0.36 g, 2.23 mmol, 1.02 eq.) and warmed as described. The reaction was allowed to cool and then treated with N,N-dimethylethylenediamine (0.23 g, 2.63 mmol, 1.2 eq.). The reaction was treated as described in example 1 to give an orange/brown oil. The oil was purified by 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 2-carboxylic acid (2-dimethylamino-ethyl)-amide (0.81 g, 85% yield) as a faint yellow oil.

Workup

  1. custom2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (2-dimethylamino-ethyl)-amide was synthesized
  2. temperaturewarmed
  3. temperatureto cool
  4. additionThe reaction was treated
  5. customto give an orange/brown 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-2ee1795f9f37426a86eb94bcf8bec676
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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