Hydrochloric Acid → (4-(6-(3-Aminopiperidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone hydrochloride

HRID 2271906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2271906
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13]=[CH:12][C:11]([NH:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:25]5[CH:30]=[C:29]([F:31])[C:28]([OH:32])=[C:27]([Cl:33])[CH:26]=5)[CH:23]=4)[N:18]=[CH:17][C:16]=3[C:34]([CH:36]3[CH2:38][CH2:37]3)=[O:35])=[CH:10][CH:9]=2)[CH2:3]1.Cl>CO.C(OCC)C>[ClH:33].[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13]=[CH:12][C:11]([NH:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:25]5[CH:30]=[C:29]([F:31])[C:28]([OH:32])=[C:27]([Cl:33])[CH:26]=5)[CH:23]=4)[N:18]=[CH:17][C:16]=3[C:34]([CH:36]3[CH2:38][CH2:37]3)=[O:35])=[CH:10][CH:9]=2)[CH2:3]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 66715684(4-(6-(3-Aminopiperidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxy phenyl)quinolin-3-yl)(cyclopropyl)methanone

Produkt 1

HCID 66716241(4-(6-(3-Aminopiperidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone hydrochlorideAusbeute 175,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

(4-(6-(3-aminopiperidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone (12 mg, 0.02 mmol) was suspended in methanol (1 mL) at 0° C. followed by dropwise addition of HCl in diethyl ether (2 M) until complete dissolution of the solid was observed. The solvent was removed under reduced pressure to afford the desired product (10 mg, 80%) as an orange-red solid: 1H NMR (500 MHz, MeOD) δ 9.39 (s, 1H), 8.27-8.19 (m, 2H), 8.13 (br s, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.72 (dd, J=9.2, 2.7 Hz, 1H), 7.21-7.07 (m, 3H), 4.52 (d, J=10.8 Hz, 1H), 4.06-3.98 (m, 1H), 3.43-3.31 (m, 3H), 2.90-2.81 (m, 1H), 2.28-2.16 (m, 1H), 2.01-1.92 (m, 1H), 1.80-1.68 (m, 2H), 1.31-1.15 (m, 4H). ESI MS m/z 532 [C29H27ClFN5O2+H]+; HPLC 98.7% (AUC), tR=10.82 min.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0c9c213d81bb48bb9bbbbe3542bd475e
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120749B2

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