![](/CAS/GIF/851169-48-7.gif)
1-(2-furyl)-N~1~,N~1~-dimethyl-1,2-ethanediamine(SALTDATA: FREE) synthesis
- Product Name:1-(2-furyl)-N~1~,N~1~-dimethyl-1,2-ethanediamine(SALTDATA: FREE)
- CAS Number:851169-48-7
- Molecular formula:C8H14N2O
- Molecular Weight:154.21
![1-(2-furyl)-N~1~,N~1~-dimethyl-1,2-ethanediamine(SALTDATA: FREE)](/CAS/GIF/851169-48-7.gif)
851169-48-7
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![4-Chloro-Pyrrolo[1,2-b]pyridazine-3-carbonitrile](/CAS/20180527/GIF/1263420-00-3.gif)
1263420-00-3
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![Pyrrolo[1,2-b]pyridazine-3-carbonitrile, 4-[[2-(dimethylamino)-2-(2-furanyl)ethyl]amino]-](/CAS/20210305/GIF/1263419-29-9.gif)
1263419-29-9
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Yield:1263419-29-9 86%
Reaction Conditions:
with N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide at 20;
Steps:
23
To a solution of 4-chloropyrrolo[l,2-b]pyridazine-3-carbonitrile (15g) (0.177 g, 0.997 mmol) in DMF (2.5 mL) was added at room temperature l-(furan-2-yl)-Nl,Nl-dimethylethane- 1,2-diamine (49g) (OTAVA 7020410165 , 0.25 g, 1.62 mmol), DIPEA (0.87 mL, 5 mmol) and stirred at room temperature overnight. The reaction was quenched with water (10 mL) and extracted with ethyl acetate (10 mL). The aqueous layer was separated and extracted with ethyl acetate (2 x 10 mL). The organic layers were combined washed with water (2 x 10 ml), brine (10 mL), dried, filtered and concentrated in vacuum. The residue obtained was purified by flash column chromatography (silica gel 12g, eluting with 0-100% ethyl acetate in hexanes) to furnish 4-(2-(dimethylamino)-2-(furan-2-yl)ethylamino)pyrrolo[l,2-b]pyridazine-3-carbonitrile (49h) as a white semisolid, which was crystallized from ether/hexane to furnish (0.253 g, 86%) white, crystalline solid; MP 106.90C; 1H NMR (300 MHz, DMSO) δ 7.94 (s, IH), 7.76 - 7.71 (m, IH), 7.65 (dd, J= 0.7, 1.8, 2H), 7.04 (dd, J= 1.6, 4.5, IH), 6.70 (dd, J= 2.7, 4.4, IH), 6.44 (dd, J = 1.8, 3.2, IH), 6.39 (d, J= 3.0, IH), 4.09 (m, 3H), 2.16 (s, 6H); MS (ES+) 588.9 (2M), (ES-) 329.9 (M+Cl); Analysis: Calcd for C16H17N5O: C, 65.07; H, 5.80; N, 23.71; Found: C, 65.23; H, 5.98; N, 23.64.
References:
WO2011/14817,2011,A1 Location in patent:Page/Page column 110; 111