Реакция #511674

Уравнение реакции

4-(2-(dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-amine

methyl thiophene-2-carbimidothioate hydroiodide

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title compound 9

N-(4-(2-(dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-thiophene-2-carboximidamide

Условия реакции

Обработка

1. 1
   workup.WAITAfter 20 hours
2. 2
   Другоеargon was bubbled through the mixture, which
3. 3
   Концентрированиеwas then concentrated
4. 4
   Другоеto afford a residue
5. 5
   ДругоеThe residue was then partitioned between EtOAc (100 mL) and saturated NaHCO3 (˜10 mL) solution
6. 6
   ЭкстракцияThe aqueous layer (pH ˜9) was further extracted with EtOAc
7. 7
   Промывкаthe combined organic layers were washed with brine
8. 8
   Сушкаdried (Na2SO4)
9. 9
   Фильтрацияfiltered
10. 10
    Концентрированиеconcentrated
11. 11
    Другоеto yield a yellow residue
12. 12
    ДругоеPurification on silica gel (dry chromatography, eluting with 5-7.5% (2M NH3 MeOH)/CH2Cl2)

Методика

To a stirred ethanolic solution of 4-(2-(dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-amine (0.088 g, 0.398 mmol) under an argon atmosphere was added methyl thiophene-2-carbimidothioate hydroiodide (0.227 g, 0.795 mmol). The resulting faintly cloudy yellow mixture stirred overnight at room temperature. After 20 hours, argon was bubbled through the mixture, which was then concentrated to afford a residue. The residue was then partitioned between EtOAc (100 mL) and saturated NaHCO3 (˜10 mL) solution. The aqueous layer (pH ˜9) was further extracted with EtOAc, and the combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated to yield a yellow residue. Purification on silica gel (dry chromatography, eluting with 5-7.5% (2M NH3 MeOH)/CH2Cl2) yielded the title compound 9 as a yellow residue (70 mg, 53.3%). 1H NMR (DMSO-d6) δ 7.70 (d, 1H, J=2.7 Hz), 7.57 (d, 1H, J=5.0 Hz), 7.07 (dd, 1H, J=5.0, 3.7 Hz), 6.59 (d, 1H, J=8.2 Hz), 6.30 (brs, 2H), 6.14 (s, 1H), 6.00 (d, 1H, J=8.1 Hz), 4.18-4.02 (m, 2H), 3.41-3.25 (m, 4H+H2O), 2.41 (t, 2H, J=6.7 Hz), 2.17 (s, 6H); ESI-MS (m/z, %): 331 (MH+, 100).

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