Diethylamine → 6-(4-(2-(4-Chlorobenzenesulphonylamino)ethyl)phenyl)-6-(3-pyridyl)-hex-5-enoic acid diethylamide

HRID 1490380

Reaction equation

HRID 1490380 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:21][CH2:22][CH2:23][CH2:24][C:25](O)=[O:26])=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:46]([NH:48][CH2:49][CH3:50])[CH3:47]>O1CCCC1>[CH2:46]([N:48]([CH2:49][CH3:50])[C:25](=[O:26])[CH2:24][CH2:23][CH2:22][CH:21]=[C:20]([C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][NH:11][S:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)(=[O:10])=[O:9])=[CH:19][CH:18]=1)[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[CH3:47]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 659716-(4-(2-(4-Chlorobenzenesulphonylamino)ethyl)-phenyl)-6-(3-pyridyl)hex-5-enoic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 542838606-(4-(2-(4-Chlorobenzenesulphonylamino)ethyl)phenyl)-6-(3-pyridyl)-hex-5-enoic acid diethylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of 6-(4-(2-(4-chlorobenzenesulphonylamino)ethyl)phenyl)-6-(3-pyridyl)hex-5-enoic acid are dissolved in 15 ml of tetrahydrofuran and stirred for 15 minutes with 0.49 g of carbonyldiimidazole. Then 1 ml of diethylamine is added and the mixture is refluxed for 2 hours. It is then concentrated by evaporation and the residue is taken up in ethyl acetate and dried. Finally, it is chromatographed over a silica gel column using ethyl acetate as eluant.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. concentrationIt is then concentrated by evaporation
  3. customdried
  4. customFinally, it is chromatographed over a silica gel column

Sources & evidence

ORD record
ord-9d06988d68ac4cf0a3a71af0f8392785
Source dataset
uspto-grants-1997_10
Patent number
US05681961

Linked notes

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