Hydrochloric Acid → 5-((5-Fluoropyridin-2-yl)methoxy)-2-(10-methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepin-2-yl)pyridazin-3(2H)-one hydrochloride

HRID 474980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474980
[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][C:11]2[CH:12]=[N:13][N:14]([C:18]3[CH:19]=[CH:20][C:21]4[C:30]5[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25][C:24]=5[N:23]([CH3:38])[C:22]=4[N:39]=3)[C:15](=[O:17])[CH:16]=2)=[N:7][CH:8]=1>CO.CCOCC>[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][C:11]2[CH:12]=[N:13][N:14]([C:18]3[CH:19]=[CH:20][C:21]4[C:30]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25][C:24]=5[N:23]([CH3:38])[C:22]=4[N:39]=3)[C:15](=[O:17])[CH:16]=2)=[N:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric Acid2×HCID 58093420tert-butyl 2-(4-((5-fluoropyridin-2-yl)methoxy)-6-oxopyridazin-1(6H)-yl)-10-methyl-5,8,9,10-tetrahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate

Produkt 1

HCID 668741695-((5-Fluoropyridin-2-yl)methoxy)-2-(10-methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepin-2-yl)pyridazin-3(2H)-one hydrochlorideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1.25 M HCl in MeOH (4.0 mL) was added to tert-butyl 2-(4-((5-fluoropyridin-2-yl)methoxy)-6-oxopyridazin-1(6H)-yl)-10-methyl-5,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate (55 mg, 0.11 mmol), and the resulting solution was stirred under N2 at ambient temperature for 18 h. Additional 1.25 M HCl in MeOH (2.0 mL) was added, and the resulting solution was stirred at ambient temperature for 24 h. The resulting solution was diluted with Et2O (30 mL), and the resulting solids were collected by filtration to provide the title compound (35 mg, 73%) as an off-white powder: mp 226-230° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 9.12 (s, 2H), 8.64 (d, J=3.0 Hz, 1H), 8.06 (d, J=8.0 Hz, 1H), 7.98 (d, J=2.5 Hz, 1H), 7.85 (ddd, J=11.5, 8.5, 2.5 Hz, 1H), 7.72-7.69 (m, 1H), 7.15 (d, J=8.5 Hz, 1H), 6.51 (d, J=3.0 Hz, 1H), 5.30 (s, 2H), 3.71 (s, 3H), 3.45-3.39 (m, 2H), 3.38-3.31 (m, 2H), 3.30-3.28 (m, 2H), 3.15-3.14 (m, 2H); ESI MS m/z 421 [M+H]+; HPLC (Method A) 98.8% (AUC), tR=11.6 min.

Aufarbeitung

  1. stirringthe resulting solution was stirred at ambient temperature for 24 h
  2. filtrationthe resulting solids were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-09e40487e81641f193d9c4aaea2f354b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637501B2

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