Trifluoroacetic acid → 2-(Acetylamino)-9-[(2s)-2-aminopropyl]-9h-pyrido[2,3-b]indole-3-carboxamide

HRID 421666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421666
[C:1](O)([C:3](F)(F)F)=[O:2].[NH2:8][C:9]1[C:10]([C:26]([NH2:28])=[O:27])=[CH:11][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][C@@H:22]([NH2:24])[CH3:23])[C:13]=2[N:25]=1>>[C:1]([NH:8][C:9]1[C:10]([C:26]([NH2:28])=[O:27])=[CH:11][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][C@@H:22]([NH2:24])[CH3:23])[C:13]=2[N:25]=1)(=[O:2])[CH3:3]

Komponenten

3

Edukt 2

HCID 6422Trifluoroacetic acidHCID 595136442-amino-9-[(2S)-2-aminopropyl]-9H-pyrido[2,3-b]indole-3-carboxamide

Produkt 1

HCID 249010622-(Acetylamino)-9-[(2s)-2-aminopropyl]-9h-pyrido[2,3-b]indole-3-carboxamideAusbeute 63 %

Versuchsvorschrift

xxxi-a (44 mg, 0.104 mmol) was deprotected using the TFA conditions detailed in the preparation of 30 to afford the title compound (66, 29 mg, 63%). NH4OAc standard conditions. DAD Retention time=4.98 min. M+H=326. 1H NMR (300 MHz, DMSO-d6): δ 12.27 (br s, 1H), 9.05 (br s, 1H), 8.41 (br s, 1H), 8.31 (br s, 3H), 8.03 (d, J=7.6 Hz, 1H), 7.80 (br s, 1H), 7.75 (d, J=8.2 Hz, 1H), 7.51 (dd, J=7.6, 7.6 Hz, 1H), 7.32 (dd, J=7.0, 7.0 Hz, 1H), 4.53 (br s, 2H), 3.87-3.75 (br m, 1H), 2.32 (s, 3H), 1.16 (d, J=6.5 Hz, 3H).

Quellen und Nachweise

ORD-Eintrag
ord-ad73203382c4443eb0642347326a1535
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101604B2

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