Hydrochloric Acid → (R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)butan-1-one hydrochloride

HRID 2062179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2062179
[OH:1][C@H:2]([CH2:28][CH3:29])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[OH:27])[N:12]=2)[CH2:7][CH2:6]1)=[O:4].[ClH:30].CCOCC>C(Cl)Cl>[ClH:30].[OH:1][C@H:2]([CH2:28][CH3:29])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[OH:27])[N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136121367(R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)butan-1-one

Produkt 1

HCID 136366871(R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)butan-1-one hydrochlorideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)butan-1-one (280 mg, 0.71 mmol) in CH2Cl2 under an N2 atmosphere was added a 2 M HCl solution in ether (0.355 mL, 0.71 mmol), followed by the addition of ether which resulted in the formation of precipitate which was stirred for an hour and then filtered and dried to afford (R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)butan-1-one hydrochloride (272 mg, 90%). LC/MS: m/z 393.1 (M+H)+ at 2.23 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.27 (dd, J=7.9, 1.6 Hz, 1H), 8.19 (d, J=8.4 Hz, 1H), 7.96 (m, 2H), 7.65 (m, 1H), 7.48 (m, 1H), 7.04 (m, 2H), 4.26 (dd, J=7.7, 4.8 Hz, 1H), 4.03 (m, 4H), 3.79 (m, 5H), 1.65 (m, 1H), 1.50 (m, 1H), 0.90 (t, J=7.4 Hz, 3H).

Aufarbeitung

  1. customresulted in the formation of precipitate which
  2. filtrationfiltered
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5511ee2fd0b5453a97cc77b39df04f45
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283354B2

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