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

HRID 2079267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2079267
[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) d 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) ppm.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-69f32f9a38c844d69a307f1ebbf65c5a
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928107B2

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