Reference of 23842-82-2,Some common heterocyclic compound, 23842-82-2, name is 2-Amino-5-methoxybenzonitrile, molecular formula is C8H8N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: To a solution of the appropriate amine (X1 NH2, 100 mumomicronIota) in anhydrous pyridine (600 muL) was added a 1.2M solution of the appropriate sulfonyl chloride in anhydrous pyridine (100 muL, 120 mumomicronIota) followed by DMAP (2 mg, 20 mumomicronIota). The reaction mixture was shaken at 30C for 2 hours followed by 60C for 16 hours before concentrating in vacuo and purifying by one of the four preparative HPLC methods described below. The organic gradient used for each compound is described in the following table. Preparative HPLC Method A: Phenomenex Gemini C18 250 x 21 .2 mm, 8 mum; mobile phase A: MeCN, mobile phase B: 0.225% formic acid in water. Gradient time 8 mins; flow rate 30 mL/min. Preparative HPLC Method B: Waters Sunfire C8 150 x 30 mm, 5 mum; mobile phase A: MeCN, mobile phase B: 0.225% formic acid in water. Gradient time 8 mins; flow rate 40 mL/min. Preparative HPLC Method C: YMC-Actus Triart C18 150 x 30 mm, 5 mum; mobile phase A: MeCN, mobile phase B: 0.225% formic acid in water. Gradient time 9 mins; flow rate 30 mL/min. Preparative HPLC Method D: Agela DuraShell C18 150 x 21.2 mm, 5 mum; mobile phase A: MeCN, mobile phase B: 0.225% formic acid in water. Gradient time 10 mins; flow rate 30 mL/min. The retention times quoted in the table below were obtained using one of the following three LCMS methods: LCMS Method A: XBRIDGE 50 x 2.1 mm, 5 mum; mobile phase A: 0.0375%TFA in water; mobile phase B: 0.01875% TFA in MeCN; gradient from 1 % B to 5% B at 0.60 mins, further to 100% B at 4.00 mins and finally returning to 1 % B at 4.30-4.70 mins; flow rate 0.8 mL/min. LCMS Method B: XBRIDGE 50 x 2.1 mm, 5 mum; mobile phase A: 0.0375%TFA in water; mobile phase B: 0.01875% TFA in MeCN; gradient from 10% B to 100% B at 4.00 mins and finally returning to 1 % B at 4.30-4.70 mins; flow rate 0.8 mL/min. LCMS Method C: XBRI DGE 50 x 2.1 mm, 5 mum; mobile phase A: 0.05%NH4OH in water; mobile phase B: 100% MeCN; gradient from 5% B to 100% B at 3.40 mins, hold at 100% B to 4.20 mins and finally returning to 5% B at 4.21 -4.70 mins; flow rate 0.8 mL/min. The compounds of Examples 130-175 were prepared according to the method described for Library Protocol 3 using either 2-cyanobenzensulfonyl chloride or 2-(trifluoromethyl)benzenesulfonyl chloride and the appropriate amine as described below. Where stated the title compounds were isolated as formate salts.
The synthetic route of 23842-82-2 has been constantly updated, and we look forward to future research findings.