O[CH2:2][CH2:3][NH:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:7].C(P(CCCC)CCCC)CCC.Cl.C(N(CC)CC)C>O1CCCC1>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([N:8]2[CH2:2][CH2:3][NH:4][CH2:5][C:6]2=[O:7])[CH:10]=1
Bis(1,1-dimethylethyl)diazenedicarboxylate (4.1 g, 18 mmol) in tetrahydrofuran (100 mL) was added dropwise to a stirred, cooled (0° C.) solution of 2-[(2-hydroxyethyl)amino]-N-(3-pyridinyl)acetamide (Description 142, 2.5 g, 13 mmol) and tributylphosphine (4.2 mL, 16.9 mmol) in tetrahydrofuran (300 mL) and the mixture was stirred at room temperature for 16 hours. Ethereal hydrogen chloride (1M, 10 mL) was added and the mixture was stirred at room temperature for 1 hour. Triethylamine (6 mL, 42 mmol) was added the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH/NH3(Aq.) (90:10:1), to give the title compound (800 mg, 35%). m/z (ES+) 178 (M+1).
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