Hydrochloric Acid → (R)-1-(4-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one hydrochloride

HRID 2062224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2062224
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9]1[N:18]=[C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:32])[C@H:26]([OH:31])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:21][CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:33])=[CH:14][CH:15]=2)[N:10]=1.CCOCC.[ClH:39]>C(Cl)Cl>[ClH:39].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9]1[N:18]=[C:17]([N:19]2[CH2:20][CH2:21][N:22]([C:25](=[O:32])[C@H:26]([OH:31])[CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:23][CH2:24]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:33])=[CH:14][CH:15]=2)[N:10]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric Acid2×HCID 3283Diethyl Ether2×HCID 135453120(R)-1-(4-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one

Produkt 1

HCID 136366945(R)-1-(4-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one hydrochlorideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(R)-1-(4-(2-(2-Fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one (406 mg, 0.898 mmol) was dissolved in anhydrous CH2Cl2 (3 mL) followed by the addition of Et2O (6 mL) under an N2 atmosphere. A 2.0 M HCl solution in Et2O (0.449 mL, 0.898 mmol) was added over a 2 minute period. The reaction solution changed from a clear yellow solution to a turbid white slurry. After complete addition of the HCl solution, the reaction was allowed to stir for an additional 15 minutes. The product was collected by vacuum filtration and dried under vacuum to obtain (R)-1-(4-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one hydrochloride as a white solid (403 mg, 92%). LC/MS: m/z 453.5 (M+H)+ at 2.44 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.20 (d, J=8.7 Hz, 1H), 7.71 (s, 1H), 7.60-7.60 (m, 1H), 7.50-7.44 (m, 1H), 6.99 (d, J=8.4 Hz, 1H), 6.87 (t, J=9.1 Hz, 1H), 4.36-4.33 (m, 1H), 4.25-3.67 (m, 8H), 2.57 (s, 3H), 1.83-1.71 (m, 1H), 1.49-1.35 (m, 2H), 0.91 (d, J=6.7 Hz, 6H).

Aufarbeitung

  1. filtrationThe product was collected by vacuum filtration
  2. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ccd5f70782144ef0adcbac20002502ba
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283354B2

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