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

HRID 2271908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2271908
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[CH:29]=[C:28]([F:30])[C:27]([OH:31])=[C:26]([Cl:32])[CH:25]=5)[CH:22]=4)[N:17]=[CH:16][C:15]=3[C:33]([CH:35]3[CH2:37][CH2:36]3)=[O:34])=[CH:9][CH:8]=2)[CH2:3]1.Cl>CO.C(OCC)C>[ClH:32].[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[CH:29]=[C:28]([F:30])[C:27]([OH:31])=[C:26]([Cl:32])[CH:25]=5)[CH:22]=4)[N:17]=[CH:16][C:15]=3[C:33]([CH:35]3[CH2:36][CH2:37]3)=[O:34])=[CH:9][CH:8]=2)[CH2:3]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 66716234(4-(6-(3-Aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone

Produkt 1

HCID 66716423(4-(6-(3-Aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone hydrochlorideAusbeute 276,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

(4-(6-(3-aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone (15 mg, 0.03 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 (23 mg, quant.) as a yellow-brown solid. 1H NMR (500 MHz, MeOD) δ 9.39 (s, 1H), 8.28-8.19 (m, 2H), 8.16 (br s, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.79 (dd, J=9.1, 2.7 Hz, 1H), 7.26-7.16 (m, 2H), 6.94 (d, J=9.2 Hz, 1H), 4.16-4.08 (m, 1H), 4.05-3.97 (m, 1H), 3.88-3.79 (m, 1H), 3.78-3.69 (m, 2H), 2.85 (br s, 1H), 2.64-2.53 (m, 1H), 2.34-2.21 (m, 1H), 1.25-1.15 (m, 4H). ESI MS m/z 518 [C28H25ClFN5O2+H]+; HPLC 98.1% (AUC), tR=5.13 min.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-05552504360c41208696e4b2d4521138
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120749B2

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