Reaktion #171565

Reaktionsgleichung

methanol ethyl acetate

aniline

4-(2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline

DIPEA

HATU

DMF

→

140

Ausbeute 34.0%

N-(4-(2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide

Ausbeute 34.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIt was then partitioned between ethyl acetate and water
2. 2
   Sonstigethe organic phase was collected
3. 3
   Waschenwashed with water, 1M NaOH, saturated NH4Cl, and brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated

Vorschrift

To aniline 139 (Scheme 7) (0.46 g, 1.1 mmol) in dry DMF (20 mL) was added acid 1-(phenylcarbamoyl)cyclopropanecarbpxylic acid (0.46 g, 2.2 mmol), DIPEA (0.98 mL, 5.6 mmol) and HATU (1.07 g, 2.81 mmol) and the mixture was stirred at r.t. for 18 h. It was then partitioned between ethyl acetate and water; the organic phase was collected, washed with water, 1M NaOH, saturated NH4Cl, and brine, dried (MgSO4), filtered and concentrated. Silica gel chromatography of the residue (eluent 2% methanol/ethyl acetate) afforded 140 (0.23 g, 34% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.37 (s, 1H), 9.98 (s, 1H), 8.68 (s, 1H), 8.53 (d, J=5.3 Hz, 1H), 8.40 (s, 1H), 8.31 (d, J=8.2 Hz, 1H), 7.97 (dd, J=8.2, 2.0 Hz, 1H), 7.90 (dd, J=13.1, 2.0 Hz, 1H), 7.62 (d, J=7.6, 2H), 7.53-7.46 (m, 2H), 7.30 (t, J=7.4 Hz, 2H), 7.06 (t, J=7.4 Hz, 1H), 6.66 (d, J=5.3 Hz, 1H), 5.88 (s, 1H), 4.11-3.97 (m, 4H), 1.47 (br s, 4H). MS (m/z): 597.2 (M+H).

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