Citric Acid → HCID 58306745, Verbindung

HRID 1909878

Reaktionsgleichung

Reaktionsgleichung von HRID 1909878
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[C:16]([NH:18][C@H:19]([C:21]3[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=3)[CH3:20])=[O:17])[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:44][S:45]([CH2:48][CH2:49][CH2:50][O:51][C:52](=[O:54])[CH3:53])(=[O:47])=[O:46].N12CCCN=C1CCCCC2.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[C:16]([NH:18][C@H:19]([C:21]3[CH:29]=[CH:28][C:24]([C:25](=[O:26])[NH:44][S:45]([CH2:48][CH2:49][CH2:50][O:51][C:52](=[O:54])[CH3:53])(=[O:46])=[O:47])=[CH:23][CH:22]=3)[CH3:20])=[O:17])[CH:9]=[CH:8]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 5

HCID 311Citric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 106074883-(Aminosulfonyl)propyl acetateHCID 25155194HCID 25155194, Verbindung

Produkt 1

HCID 58306745HCID 58306745, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 4-[(1S)-1-({[1-(4-chlorobenzyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoic acid (250 mg) and DMF (5 mL) was added 1,1′-carbonyldiimidazole (187 mgl) at room temperature, followed by stirring for 5 minutes, and then 3-(aminosulfonyl)propylacetate (209 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (173 μL) were added in this order, followed by stirring for 3 days. The reaction mixture was ice-cooled, and 10% aqueous citric acid (30 mL) was added thereto, followed by stirring for 30 minutes. The precipitated solid was collected by filtration and washed with cold ethanol (4 mL) to obtain 1-(4-chlorobenzyl)-N-[(1S)-1-(4-{[(3-acetoxypropyl)sulfonyl]carbamoyl}phenyl)ethyl]-1H-indole-7-carboxamide (210 mg) as a pale yellow solid.

Aufarbeitung

  1. stirringby stirring for 3 days
  2. temperaturecooled
  3. stirringby stirring for 30 minutes
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with cold ethanol (4 mL)

Quellen und Nachweise

ORD-Eintrag
ord-971e431d31584150ac9bdfa69b4bad13
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598355B2

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