[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[N:12][NH:13][N:14]=2)[N:7]=[C:6]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:28][CH3:29]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[N:14]([CH2:28][CH3:29])[N:13]=[N:12][N:11]=2)[N:7]=[C:6]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:5]=1Treat a solution of (S)-2-sec-butylamino-6-(2H-tetrazol-5-yl)-isonicotinic acid methyl ester (720 mg, 2.61 mmol) in DMF (10 mL) with potassium carbonate (541 mg, 3.92 mmol) and iodoethane (0.364 mL, 3.92 mL) at room temperature. Dilute with ethyl acetate (100 mL), wash with water (twice), saturated aqueous sodium chloride, dry (sodium sulfate) and concentrate to give approximately a 1:1 mixture of the two title compounds which are used directly in the next step without further purification.
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