Reaktion #1755641

Reaktionsgleichung

compound 61

1-(2-(1-Methylpiperidin-2-yl)ethyl)-1H-indol-5-amine

methyl thiophene-2-carbimidothioate hydroiodide

→

compound 62

Ausbeute 46.2%

N-(1-(2-(1-Methylpiperidin-2-yl)ethyl)-1H-indol-5-yl)thiophene-2-carboximidamide

Ausbeute 46.2%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeArgon was bubbled through the mixture for 20 minutes
2. 2
   Einengenit was concentrated
3. 3
   Sonstigeto give brownish oil
4. 4
   SonstigeThis residue was partitioned between CH2Cl2 (50 mL) with 10% MeOH and saturated sodium bicarbonate (20 mL)
5. 5
   ExtraktionThe aqueous layer was extracted with an additional CH2Cl2 (50 mL)
6. 6
   WaschenThe combined organic layers were washed with brine
7. 7
   Trocknendried over sodium sulfate
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto give a brown residue which

Vorschrift

A solution of compound 61 (235 mg, 0.91 mmol) in EtOH (10 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (520 mg, 1.83 mmol) and stirred overnight at room temperature. Argon was bubbled through the mixture for 20 minutes then it was concentrated to give brownish oil. This residue was partitioned between CH2Cl2 (50 mL) with 10% MeOH and saturated sodium bicarbonate (20 mL). The aqueous layer was extracted with an additional CH2Cl2 (50 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to give a brown residue which was subjected to flash chromatography on silica gel (MeOH:CH2Cl2, 5:95 to 2M NH3 in MeOH:CH2Cl2, 1:9) to give compound 62 (154 mg, 46.1%) as a yellow solid. 1H NMR (DMSO-d6) δ 7.71 (d, J=2.9 Hz, 1H), 7.58 (d, J=5.1 Hz, 1H), 7.37-7.30 (m, 2H), 7.10-7.08 (m, 1H), 6.98 (s, 1H), 6.70 (dd, J=1.5, 6.9 Hz, 1H), 6.31 (d, J=3.0 Hz, 1H), 6.25 (brs, 2H), 4.15 (t, J=7.5 Hz, 2H), 2.79-2.75 (m, 1H), 2.19 (s, 3H), 2.05-1.15 (m, 10H); ESI-MS (m/z, %): 367 (M+1,50), 184 (M+2, 100); ESI-HRMS calculated for C21H27N4S (MH+): 367.1966, observed: 367.1937.

Quelle