N,N-dimethyl-2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxamide → (R)-N,N-dimethyl-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]oxazole-6-carboxamide

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Reaktionsgleichung

[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[CH:14]=[CH:13][C:8]2[NH:9][C:10](=S)[O:11][C:7]=2[CH:6]=1)=[O:4].Cl.Cl.[NH:18]1[CH2:22][CH2:21][C@@H:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:19]1>C1(C)C(C)=CC=CC=1.ClCCl>[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[CH:14]=[CH:13][C:8]2[N:9]=[C:10]([N:18]3[CH2:22][CH2:21][C@@H:20]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]4)[CH2:19]3)[O:11][C:7]=2[CH:6]=1)=[O:4]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

N,N-Dimethyl-2-thioxo-2,3-dihydrobenzo[d]oxazole-6-carboxamide (Example 92C, 44 mg, 0.119 mmol) and (R)-1-(pyrrolidin-3-yl)piperidine dihydrochloride (Reference Example 5c, 54 mg, 0.238 mmol) were combined in xylene (1 mL) and heated to 150° C. for 30 minutes. The mixture was diluted with dichloromethane, washed with water, and the organic layer was absorbed on silica gel. The crude mixture was purified by silica gel chromatography eluting with a gradient of methanol in dichloromethane (2-20%) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.43-1.53 (m, 2 H) 1.59-1.70 (m, 4 H) 1.91-2.07 (m, 1 H) 2.23-2.35 (m, 1 H) 2.40-2.62 (m, 4 H) 2.93-3.13 (m, 7 H) 3.41-3.51 (m, 1 H) 3.55-3.66 (m, 1 H) 3.80-3.90 (m, 1 H) 3.96 (dd, J=10.00, 7.29 Hz, 1 H) 7.22-7.28 (m, 1 H) 7.30-7.35 (m, 1 H) 7.37-7.40 (m, 1 H); MS (ESI+) m/z 343.0 (M+H)+.

Aufarbeitung

washwashed with water
customthe organic layer was absorbed on silica gel
customThe crude mixture was purified by silica gel chromatography
washeluting with a gradient of methanol in dichloromethane (2-20%)

Quellen und Nachweise

ORD-Eintrag: ord-06bcc887dc354e85b36daae3f60405b9
Quelldatensatz: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08153813B2

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