Oxalyl chloride → Methyl 4-({[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)phenyl]sulfonyl}amino)benzoate

HRID 926070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926070
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18](O)=[O:19])(=[O:14])=[O:13])=[CH:7][CH:6]=1)=[O:4].C(Cl)(=O)C(Cl)=O.[NH2:30][C:31]1[S:32][C:33]2[CH2:60][CH2:59][CH2:58][CH2:57][C:34]=2[C:35]=1[C:36]([NH:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][C:47]2[CH:56]=[CH:55][C:50]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][CH:48]=2)=[CH:41][CH:40]=1)=[O:37]>CN(C=O)C.ClCCl.N1C=CC=CC=1>[CH3:54][O:53][C:51]([C:50]1[CH:49]=[CH:48][C:47]([CH2:46][CH2:45][C:42]2[CH:41]=[CH:40][C:39]([NH:38][C:36]([C:35]3[C:34]4[CH2:57][CH2:58][CH2:59][CH2:60][C:33]=4[S:32][C:31]=3[NH:30][C:18]([C:17]3[CH:16]=[C:15]([S:12]([NH:11][C:8]4[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=4)(=[O:14])=[O:13])[CH:23]=[CH:22][CH:21]=3)=[O:19])=[O:37])=[CH:44][CH:43]=2)=[CH:56][CH:55]=1)=[O:52]

Komponenten

7

Edukt 3

HCID 65578Oxalyl chlorideHCID 250374323-{[4-(Methoxycarbonyl)phenyl]sulfamoyl}benzoic acidHCID 68207883Methyl 4-[2-(4-{[(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate

Produkt 1

HCID 71238552Methyl 4-({[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)phenyl]sulfonyl}amino)benzoateAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 347 mg of 3-{[4-(methoxycarbonyl)phenyl]sulfamoyl}benzoic acid, 0.090 mL of oxalyl chloride, 3.0 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 3.0 mL of dichloromethane was added to a mixture of 0.071 mL of pyridine, 300 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 505 mg of methyl 4-({[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)phenyl]sulfonyl}amino)benzoate as a yellow foamed solid. ESI+: 752

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionA mixture of the
  3. customobtained crude product and 3.0 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-b7de52aefef3446a99aef2350f9a4d3e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284295B2

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