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Trifluoroacetic acid → HCID 86680808, Verbindung

HRID 2402403
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2402403
O[C@@:2]1([C:16]2[S:17][C:18]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([NH:28][C:29]4[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][N:30]=4)[N:22]=3)=[CH:19][N:20]=2)[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2.[N-:39]=[N+:40]=[N-:41].[Na+].C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:39]([C:2]1([C:16]2[S:17][C:18]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([NH:28][C:29]4[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][N:30]=4)[N:22]=3)=[CH:19][N:20]=2)[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2)=[N+:40]=[N-:41]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 70978025(S)-methyl 5-hydroxy-5-(5-(4-methyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)pyridin-2-yl)thiazol-2-yl)-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Produkt 1

HCID 86680808HCID 86680808, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a mixture of (S)-methyl 5-hydroxy-5-(5-(4-methyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)pyridin-2-yl)thiazol-2-yl)-5,6,7,8-tetrahydronaphthalene-2-carboxylate (100 mg, 0.185 mmol) and sodium azide (36.1 mg, 0.555 mmol) in DCM (2 mL) at rt was added TFA (0.016 mL, 0.203 mmol) dropwise and the mixture was stirred at rt for 16 h, after which time the reaction was heated to 40° C. for 5 days. The mixture was filtered, and the filtrate was concentrated under reduced pressure to give crude methyl 5-azido-5-(5-(4-methyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)pyridin-2-yl)thiazol-2-yl)-5,6,7,8-tetrahydronaphthalene-2-carboxylate as a brown oil, which was used as such for the following transformation. MS ESI calcd for C27H22F3N7O2S [M+H]+ 566, found 566.

Aufarbeitung

  1. temperatureafter which time the reaction was heated to 40° C. for 5 days
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-929ea55452c64cc9ad2d84a755d4e63a
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08796310B2

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