With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.147611-03-8,tert-Butyl 7-azaspiro[3.5]nonan-2-ylcarbamate,as a common compound, the synthetic route is as follows.
4-{[(Imidazo[1,2-a]pyridine-6-carbonyl)-amino]-methyl}-benzenesulfonyl chloride (450 mg, 0.13 mmol) was added to a mixture of (7-aza-spiro[3.5]non-2-yl)-carbamic acid tert-butyl ester (47.8 mg, 0.19 mmol) and triethyl amine (0.09 ml,, 0.64 mmol) in methylene chloride (2 mL). The reaction mixture was stirred at rt for 24 h and then concentrated to dryness under vacuum to give the crude title product. The residue was purified by preparative HPLC (column: Gemini-NX, 3x 10 cm, 10 um, detection: UV 254 nm; mobile phase A: H2O containing 0.1% NuH4OmicronEta, mobile phase B: Acetonitrile; flow rate: 60 mL/min, gradient: 0-1 min 5% B, 1-10 min.5-50% B, 10-11 min 50% B, 11-11.2 min.50-95% B, 11.2-13 min.95% B, 13-13.2 min 95-5% B, 13.2-15 min.5% B), then by preparative chiral SFC to remove a small amount of contaminating [7-(3-{[(imidazo[ 1 ,2-a]pyridine-6-carbonyl)-amino]-methyl}-benzenesulfonyl)-7-aza-spiro[3.5]non-2-yl]-carbamic acid tert-butyl ester (Column: Lux Cellulose-3, 3 x 25 cm, 5 um; detection: UV 254 nm, mobile phase A: CO2, mobile phase B: MeOH containing 01 % NH4OH; flow rate: 200 mL/min; gradient: isocratic, A:B = 75:25). Isolation and concentration of the appropriate fractions afforded the desired product as a white solid (31 mg, 42%). 1H NMR (400 MHz, DMSO-d6) delta 9.21 (t,J = 6.0 Hz.1H).9.17 (s, 1H), 8.07 (s, 1H), 7.73-7.65 (m,4H), 7.63 (d,./=9.5 Hz, 1H), 7.58 (d,J= 8.1 Hz, 2H), 7.01 (d,J=7.8 Hz, 1 H), 4.61 (d,./ = 5.9 Hz, 2H), 3.88-3.77 (m, 1H), 2.86 (t,./= 5.4 Hz, 2H), 2.78 (t,./= 5.3 Hz, 2H), 1.98-1.88 (m, 3H), 1.60-1.47 (m, 5H), 133 (s, 9H) LC/MS (Method K, ESI): RT = 4.11 min, m/z= 554.2 [M + H]+
147611-03-8, As the paragraph descriping shows that 147611-03-8 is playing an increasingly important role.
Reference：
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; DRAGOVICH, Peter; GOSSELIN, Francis; GUNZNER-TOSTE, Janet; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZAK, Mark; ZHANG, Yamin; ZHAO, Guiling; ZHENG, Xiaozhang; YUEN, Po-Wai; WO2013/127266; (2013); A1;,
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