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

HRID 474970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474970
[ClH:1].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:17]=[CH:18][C:19]3[C:28]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23][C:22]=4[N:21]([CH3:36])[C:20]=3[N:37]=2)[C:12](=[O:38])[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[ClH:1].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:17]=[CH:18][C:19]3[C:28]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23][C:22]=4[N:21]([CH3:36])[C:20]=3[N:37]=2)[C:12](=[O:38])[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 58093462tert-butyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-10-methyl-5,8,9,10-tetrahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate

Produkt 1

HCID 668736444-(Benzyloxy)-1-(10-methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepin-2-yl)pyridin-2(1H)-one hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.25 M HCl in MeOH (4 mL) was added to tert-butyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-10-methyl-5,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate (0.12 g, 0.24 mmol) and the resulting solution was stirred under N2 at ambient temperature for 18 h. The solution was concentrated to dryness to provide the title compound (0.11 g, quant.) as an orange solid: mp 180-185° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 9.19 (s, 2H), 8.02 (d, J=8.5 Hz, 1H), 7.79 (d, J=7.5 Hz, 1H), 7.48-7.41 (m, 4H), 7.38 (d, J=7.5 Hz, 1H), 7.30 (d, J=8.0 Hz, 1H), 6.16 (dd, J=7.5, 2.5 Hz, 1H), 5.98 (d, J=2.5 Hz, 1H), 5.16 (s, 2H), 3.73 (s, 3H), 3.39-3.38 (m, 2H), 3.33-3.31 (m, 2H), 3.30-3.28 (m, 2H), 3.14 (t, J=5.5 Hz, 2H); ESI MS m/z 401 [M+H]+; HPLC (Method A)>99% (AUC), tR=13.9 min.

Aufarbeitung

  1. concentrationThe solution was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b7c2c0bd4a0e4821ba57effb077150f7
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637501B2

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