Oxalyl chloride → HCID 178464524, Verbindung

HRID 926053

Reaktionsgleichung

Reaktionsgleichung von HRID 926053
[CH2:1]([N:3]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH2:17]1)[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11])(=[O:6])=[O:5])[CH3:2].C(Cl)(=O)C(Cl)=O.[NH2:32][C:33]1[S:34][C:35]2[CH2:62][CH2:61][CH2:60][CH2:59][C:36]=2[C:37]=1[C:38]([NH:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][C:49]2[CH:58]=[CH:57][C:52]([C:53]([O:55][CH3:56])=[O:54])=[CH:51][CH:50]=2)=[CH:43][CH:42]=1)=[O:39]>CN(C=O)C.ClCCl.N1C=CC=CC=1>[CH2:1]([N:3]([C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:18][CH2:17]1)[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([NH:32][C:33]1[S:34][C:35]2[CH2:62][CH2:61][CH2:60][CH2:59][C:36]=2[C:37]=1[C:38]([NH:40][C:41]1[CH:42]=[CH:43][C:44]([CH2:47][CH2:48][C:49]2[CH:50]=[CH:51][C:52]([C:53]([O:55][CH3:56])=[O:54])=[CH:57][CH:58]=2)=[CH:45][CH:46]=1)=[O:39])=[O:11])(=[O:6])=[O:5])[CH3:2]

Komponenten

7

Edukt 3

HCID 65578Oxalyl chlorideHCID 68207883Methyl 4-[2-(4-{[(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoateHCID 178464526HCID 178464526, Verbindung

Produkt 1

HCID 178464524HCID 178464524, VerbindungAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 319 mg of 3-{ethyl[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoic acid, 0.10 mL of oxalyl chloride, 2.5 mL of dichloromethane, and one drop of DMF was stirred at room temperature for 2 hours, and then the reaction mixture was concentrated under reduced pressure. A mixture of the obtained crude product and 2.5 mL of dichloromethane was added to a mixture of 0.050 mL of pyridine, 250 mg of methyl 4-[2-(4-{[(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate, and 2.5 mL of dichloromethane, followed by stirring at room temperature overnight. The reaction mixture was purified by silica gel column chromatography (hexane-chloroform) to obtain 320 mg of methyl 4-(2-{4-[({2-[(3-{ethyl[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoate as a yellow foamed solid.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionA mixture of the
  3. customobtained crude product and 2.5 mL of dichloromethane
  4. stirringby stirring at room temperature overnight
  5. customThe reaction mixture was purified by silica gel column chromatography (hexane-chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-eed63bc3730d403ba970f284b4fe4773
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284295B2

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