Triethylamine → 5-[4-(2-Fluoro-3-methyl-benzyl)-piperazin-1-yl]-quinazoline-2,4-diamine

HRID 1015397

Reaktionsgleichung

C(N(CC)CC)C.[N:8]1([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[C:16]([NH2:25])=[N:17][C:18]([NH2:24])=[N:19]3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[F:26][C:27]1[C:34]([CH3:35])=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29]Br>CN(C)C=O>[F:26][C:27]1[C:34]([CH3:35])=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29][N:11]1[CH2:12][CH2:13][N:8]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[C:16]([NH2:25])=[N:17][C:18]([NH2:24])=[N:19]3)[CH2:9][CH2:10]1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

In an 8 mL vial with stir bar, triethylamine (40 mg; 0.4 mmol) was added to a mixture of 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and 2-fluoro-3-methylbenzyl bromide (54 mg; 0.27 mmol) in dimethylformamide and heated to 60° C. for 16 hours. Mixture was quenched with 1 mL of 1N NaOH and after 1.5 hours solids were collected by filtration and triturated with ethanol to obtain 37 mg of title compound. (51% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.86 (s, 1H), 7.2 (m, 3H), 7.07 (t, J=7.6 Hz, 1H), 6.95 (dd, J=8.4, 0.8 Hz, 1H), 6.84 (dd, J=7.6, 0.8 Hz, 1H), 5.90 (br s, 2H), 3.59 (s, 2H), 2.98 (d, J=11.2 Hz, 2H), 2.89 (d, J=12.0 Hz, 2H), 2.81 (t, J=9.6 Hz, 2H), 2.313 (t, J=9.2 Hz, 2H), 2.24 (s, 3H). ESIMS+367.6 m/z

Aufarbeitung

customMixture was quenched with 1 mL of 1N NaOH and after 1.5 hours solids
filtrationwere collected by filtration
customtriturated with ethanol

Quellen und Nachweise

ORD-Eintrag: ord-8ab1d44075bb4fe3b5a7c3142a6181c0
Quelldatensatz: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07985755B2

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