Hydrochloric Acid → (S)-4-(Benzyloxy)-1-(1-(2-(3-fluoropyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochloride

HRID 2387494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2387494
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C@H:28]([F:31])[CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:32])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:33].C(OCC)C>C(Cl)Cl>[ClH:33].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C@H:28]([F:31])[CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:32])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 25054547(S)-4-(Benzyloxy)-1-(1-(2-(3-fluoropyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one

Produkt 1

HCID 68456200(S)-4-(Benzyloxy)-1-(1-(2-(3-fluoropyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochlorideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (S)-4-(benzyloxy)-1-(1-(2-(3-fluoropyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (56 mg, 0.12 mmol) in CH2Cl2 (1.5 mL) was treated with anhydrous HCl in diethyl ether (0.12 mL, 0.12 mmol, 1.0 M). The reaction mixture was stirred at ambient temperature for 2 h, and then the solids were collected by filtration and dried to yield the title compound (51.4 mg, 85%) as a white powder: mp 197-200° C.; 1H NMR (500 MHz, DMSO-d6) δ 10.62-10.50 (m, 1H), 8.25 (s, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.80 (s, 1H), 7.61 (d, J=7.5 Hz, 1H), 7.48-7.42 (m, 5H), 7.39-7.36 (m, 1H), 6.13 (dd, J=7.5, 3.0 Hz, 1H), 5.99 (d, J=2.5 Hz, 1H), 5.54-5.39 (m, 1H), 5.16 (s, 2H), 4.87-4.82 (m, 2H), 3.81-3.53 (m, 4H), 3.55-3.20 (m, 2H, overlapping with H2O peak), 2.14-2.01 (s, 2H); ESI MS m/z 433 [M+H]+; HPLC (Method A)>99% (AUC), tR=14.4 min; optical rotation [α]22.5D-8.4° (c 0.095, Methanol).

Aufarbeitung

  1. filtrationthe solids were collected by filtration
  2. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0175d4cb26e14a5292c5b081bc1ebee9
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268868B2

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