Trifluoroacetic acid → HCID 86698615, Verbindung

HRID 1054611Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054611
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][C:27]=3[Cl:28])[NH:24][CH:23]=[C:22]4[C:29]([OH:31])=[O:30])=[CH:15][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:28][C:27]1[CH:26]=[C:25]2[C:21]([C:22]([C:29]([OH:31])=[O:30])=[CH:23][NH:24]2)=[CH:20][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86698614HCID 86698614, Verbindung

Produkt 1

HCID 86698615HCID 86698615, VerbindungAusbeute 129,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 5-{4-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]phenyl}-6-chloro-1H-indole-3-carboxylic acid (15 mg, 0.0341 mmol) in dichloromethane (2 mL) was added TFA (0.213 g, 1.87 mmol) and the resulting mixture was stirred for 45 min at room temperature. The reaction mixture was concentrated in vacuo to give 6-chloro-5-[4-(pyrrolidin-3-yl)phenyl]-1H-indole-3-carboxylic acid (15 mg) as an off-white solid. MS (ES+) 341.0 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 11.99 (br, 1 H), 8.92 (br, 1 H), 8.09 (d, 1 H), 7.94 (s, 1 H), 7.65 (s, 1 H), 7.43 (m, 4 H), 3.70 (m, 1 H), 3.50 (m, 4 H), 3.17 (m, 1 H), 2.04 (m, 1 H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-04a18949ba9e428ba2e51847c80532fe
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394285B2

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