3-Pyridinepropanol → N-(6-(2-(3-(pyridin-3-yl)propoxy)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

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Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH2:28][CH2:29][OH:30])[CH:22]=1>N1C=CC=CC=1>[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH2:28][CH2:29][O:30][C:2]2[N:7]=[C:6]([C:8]3[CH:20]=[CH:19][C:11]4[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=4[CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

N-(6-(2-Chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (59.4 mg, 195 μmol) and 3-pyridinepropanol (0.25 mL, 1.9 mmol) were suspended in pyridine (0.80 mL) in a microwave vial, which was then sealed and heated in a microwave (CEM brand) at 120° C. and 300 watts using a ramp time of 5 minutes and a run time of 20 minutes. The reaction was cooled to RT, concentrated, and purified on HPLC (10% to >95% MeCN/water with 0.1% TFA over 40 minutes) to afford N-(6-(2-(3-(pyridin-3-yl)propoxy)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide. MS (ESI pos. ion) m/z: 406. Calculated exact mass for C21H19N5O2S: 405. 1H NMR (400 MHz, DMSO-d6): 12.51 (s, 1H), 8.83 (d, J=5.5 Hz, 2H), 8.71 (d, J=5.0 Hz, 1H), 8.64 (d, J=5.5 Hz, 1H), 8.39 (d, J=8.0 Hz, 1H), 8.25 (d, J=8.5 Hz, 1H), 7.84-7.89 (m, 2H), 7.75 (d, J=5.0 Hz, 1H), 4.47 (t, J=7.5 Hz, 2H), 2.98 (t, J=7.5 Hz, 2H), 2.23 (s, 3H), 2.17-2.22 (m, 2H).

Aufarbeitung

customwas then sealed
customa ramp time of 5 minutes
customa run time of 20 minutes
temperatureThe reaction was cooled to RT
concentrationconcentrated
custompurified on HPLC (10% to >95% MeCN/water with 0.1% TFA over 40 minutes)

Quellen und Nachweise

ORD-Eintrag: ord-5c88cf3de0bb41eda6136b6b1f4042a9
Quelldatensatz: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07928140B2

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