8-BENZYLOXY-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

25 g of 2-amino-3-benzyloxypyridine (124.8 mmol, 1 equivalent) were dissolved in 781 ml of ethanol, 102.7 g of ethyl 2-chloroacetoacetate (624.2 mmol, 5 equivalents) and 15 g of 4 A molecular sieve were added and the mixture was heated at reflux (bath temperature 100° C.) for 2 d. Then, the mixture was concentrated and excess ethyl 2-chloroacetoacetate was distilled off on a rotary evaporator using dry ice cooling. The residue was purified by silica gel chromatography (mobile phase cyclohexane:ethyl acetate=9:1, 4:1). This gave 20.81 g of the title compound (54percent of theory).10693] LC-MS (Method 2): R=1.12 mm10694] MS (ESpos): mlz=311 (M+H)10695] ‘H-NMR (400 MHz, DMSO-d5): ö=1.35 (t, 3H), 2.59 (s, 3H), 4.34 (q, 2H), 5.32 (s, 2H), 7.01-7.09 (m, 2H), 7.33-7.48 (m, 3H), 7.52 (d, 2H), 8.81-8.86 (m, 1H).Example 29A Example 23A 25 g of 2-amino-3-benzyloxypyridine (124.8 mmol, 1 equivalent) were dissolved in 781 ml of ethanol, 102.7 g of ethyl 2-chloroacetoacetate (624.2 mmol, 5 equivalents) and 15 g of 4 A molecular sieve were added and the mixture was heated at reflux (bath temperature 100° C.) for 2 d. Then, the mixture was concentrated and excess ethyl 2-chloroacetoacetate was distilled off on a rotary evaporator using dry ice cooling. The residue was purified by silica gel chromatography (mobile phase cyclohexane:ethyl acetate=9:1, 4:1). This gave 20.81 g of the title compound (54percent of theory).10693] LC-MS (Method 2): R=1.12 mm10694] MS (ESpos): mlz=311 (M+H)10695] ‘H-NMR (400 MHz, DMSO-d5): ö=1.35 (t, 3H), 2.59 (s, 3H), 4.34 (q, 2H), 5.32 (s, 2H), 7.01-7.09 (m, 2H), 7.33-7.48 (m, 3H), 7.52 (d, 2H), 8.81-8.86 (m, 1H).

Molecular Weight:310.3
XLogP3:4.2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:310.13174244
Monoisotopic Mass:310.13174244
Topological Polar Surface Area:52.8
Heavy Atom Count:23
Complexity:398
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes