Hydrochloric Acid → 1-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-2(1H)-one hydrochloride

HRID 882038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882038
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=4)=[CH:13][C:12]3=[O:27])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:28][N:29](C(OC(C)(C)C)=O)[CH2:30][CH2:31][C:3]1=2.[ClH:39]>CO.CCOCC>[ClH:39].[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][N:18]=4)=[CH:13][C:12]3=[O:27])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:28][NH:29][CH2:30][CH2:31][C:3]1=2

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 86667080tert-Butyl 9-methyl-2-(2-oxo-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-1(2H)-yl)-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylate

Produkt 1

HCID 679710441-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-2(1H)-one hydrochlorideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

tert-Butyl 9-methyl-2-(2-oxo-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-1(2H)-yl)-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (82 mg, 0.16 mmol) was treated with 1.25 M HCl in MeOH (5.0 mL), and the resulting solution was stirred at ambient temperature for 18 h. The solution was diluted with Et2O, and the resulting solids were collected by filtration to provide the title compound (55 mg, 76%) as a yellow solid: 298-302° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 9.30 (br s, 1H), 9.15 (t, J=1.0 Hz, 1H), 8.42-8.34 (m, 2H), 8.13 (d, J=8.0 Hz, 1H), 8.08 (d, J=7.0 Hz, 1H), 7.49 (d, J=8.5 Hz, 1H), 7.32 (d, J=2.0 Hz, 1H), 7.13 (dd, J=7.0, 2.0 Hz, 1H), 4.39 (s, 2H), 3.74 (s, 3H), 3.60-3.51 (m, 2H), 3.15 (t, J=6.0 Hz, 2H); ESI MS m/z 426 [M+H]+; HPLC (Method A) 98.8% (AUC), tR=13.7 min.

Aufarbeitung

  1. filtrationthe resulting solids were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-abad584abf9c412ca5b4cc38e9c5c9e4
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993765B2

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