Continuously updated synthesis method about N,N-Dimethylsulfamide

According to the analysis of related databases, 3984-14-3, the application of this compound in the production field has become more and more popular.

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 3984-14-3 as follows. 3984-14-3

Step 16: Synthesis of N-[17-[2-(3-isopropylpyrazo]-l-yl)-7-methoxy-8-methylquinolin- 4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.Cf’6]octadec-7-ene-4- carbonyl](dimethylamino)sulfonamide (29).; A mixture of 27 (181 mg, 0.29 mmol) and CDI (117 mg, 0.72 mmol) in dry THF (15 mL) was heated at reflux under nitrogen for 50 min. LCMS analysis showed one peak of the intermediate 28, which if needed, can be isolated by column chromatography or can be reacted with the appropriate sulfonamide in a one- pot reaction. The reaction mixture was cooled down to room temperature and dimethylaminosulfonamide (98 mg, 0.79 mmol) was added. Then, DBU (141 mg, 0.92 mmol) was added and the reaction mixture was heated to 550C. After 12 h, the solvent was evaporated, and the residue partitioned between AcOEt and acidic water (pH = 4). The organic layer was EPO dried (Na2SO4) and evaporated under reduced pressure to give a crude material, which was purified by column chromatography (AcOEtZCH2Cb, 25:75) to give 70 mg (33 %) of the target compound 29 as a white powder: m/z = 736 (M+H)+. 1H NMR (CDCl3): 1.20-1.50 (m, 10H), 1.60- 1.75 (m, IH), 1.79-1.91 (m, 2H), 1.92-2.03 (m, IH), 2.19-2.48 (m, 3H), 2.52-2.63 (m, 5H), 2.89-2.96 (m, 7H), 3.03 (s, 3H), 3.04-3.14 (m, IH), 3.35-3.42 (m, 2H), 3.97 (s, 3H), 4.60 (dt, J = 13.2 Hz, J = 2.2 Hz, IH), 5.05 (t, / = 10.4 Hz, IH), 5.26-3.35 (m, IH), 5.64-5.70 (m, IH), 6.26 (s, IH), 6.32 (d, J = 2.5 Hz, IH), 7.11-7.15 (m, IH), 7.30 (s, IH), 7.95 (d, / = 9.1 Hz, IH), 8.69 (d, / = 2.5 Hz, IH), 10.6 (br s, IH).

According to the analysis of related databases, 3984-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14925; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics