Hydrochloric Acid → 1-(10-Methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepin-2-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one hydrochloride

HRID 474972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474972
[ClH:1].[CH3:2][N:3]1[C:7]2[CH2:8][CH2:9][N:10](C(OC(C)(C)C)=O)[CH2:11][CH2:12][C:6]=2[C:5]2[CH:20]=[CH:21][C:22]([N:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:31]=[N:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=4)=[CH:26][C:25]3=[O:40])=[N:23][C:4]1=2>CO.CCOCC>[ClH:1].[CH3:2][N:3]1[C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[C:5]2[CH:20]=[CH:21][C:22]([N:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:31]=[N:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=4)=[CH:26][C:25]3=[O:40])=[N:23][C:4]1=2

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 66874026tert-butyl 10-methyl-2-(2-oxo-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-1(2H)-yl)-5,8,9,10-tetrahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate

Produkt 1

HCID 668744991-(10-Methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepin-2-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one hydrochlorideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1.25 M HCl in MeOH (3.2 mL) was added to tert-butyl 10-methyl-2-(2-oxo-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-1(2H)-yl)-5,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate (55 mg, 0.10 mmol), and the resulting solution was stirred under N2 at ambient temperature for 18 h. The solution was diluted with MeOH (2.2 mL) and Et2O (25 mL), and the resulting solids were collected by filtration to provide the title compound (37 mg, 76%) as a yellow powder: mp 320-325° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 9.28 (s, 2H), 9.21 (d, J=2.0 Hz, 1H), 8.50 (dd, J=8.5, 2.0 Hz, 1H), 8.10-8.04 (m, 3H), 7.41 (d, J=8.0 Hz, 2H), 7.03 (d, J=1.5 Hz, 1H), 6.85 (dd, J=7.5, 3.5 Hz, 1H), 5.98 (d, J=2.5 Hz, 1H), 3.76 (s, 3H), 3.41-3.40 (m, 2H), 3.33-3.31 (m, 2H, overlaps with solvent), 3.17 (t, J=5.5 Hz, 2H); ESI MS m/z 440 [M+H]+; HPLC (Method A) 99.0% (AUC), tR=13.6 min.

Aufarbeitung

  1. filtrationthe resulting solids were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-7fe6635a02514af29374b5871ab2360e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637501B2

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