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[ CAS No. 24016-03-3 ] {[proInfo.proName]}

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Chemical Structure| 24016-03-3
Chemical Structure| 24016-03-3
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CAS No. :24016-03-3 MDL No. :MFCD00006316
Formula : C12H12N2O Boiling Point : -
Linear Structure Formula :- InChI Key :NMCBWICNRJLKKM-UHFFFAOYSA-N
M.W : 200.24 Pubchem ID :90334
Synonyms :

Safety of [ 24016-03-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24016-03-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 24016-03-3 ]
  • Downstream synthetic route of [ 24016-03-3 ]

[ 24016-03-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 24016-03-3 ]
  • [ 609-15-4 ]
  • [ 96428-50-1 ]
YieldReaction ConditionsOperation in experiment
54% at 100℃; for 48 h; Molecular sieve Example 1A
Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate
25 g (124.8 mmol) of 2-amino-3-benzyloxypyridine were dissolved in 781 ml of ethanol, 102.7 g (624.2 mmol) of ethyl 2-chloroacetoacetate and two tablespoons of 4 A molecular sieve were added, and the reaction mixture was then heated at reflux (bath temperature 100° C.) for 2 days.
The mixture was concentrated, and excess ethyl 2-chloroacetoacetate was removed on a rotary evaporator with dry ice cooling.
The residue was purified by silica gel chromatography (mobile phase cyclohexane:ethyl acetate gradient 9:1, 4:1).
This gave 20.81 g of the target compound (54percent of theory, purity 99percent).
LC-MS (Method 2): Rt=1.12 min
MS (ESpos): m/z=311 (M+H)+
1H NMR (400 MHz, DMSO-d6): δ=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).
54% at 100℃; for 48 h; Molecular sieve Example 29A
Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate
25 g of 2-amino-3-benzyloxypyridine (124.8 mmol, 1 equivalent) were dissolved in 781 ml of ethanol, and 102.7 g of ethyl 2-chloroacetoacetate (624.2 mmol, 5 equivalents) and 15 g of 4 ? molecular sieve were added.
The mixture was heated at reflux for 2 d (bath temperature 100° C.).
The mixture was then concentrated and excess ethyl 2-chloroacetoacetate was distilled off on a rotary evaporator with 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).
LC-MS (Method 1): Rt=1.12 min
MS (ESpos): m/z=311 (M+H)+
1H NMR (400 MHz, DMSO-d6): δ=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).
54% at 100℃; for 48 h; Molecular sieve Example 23A
Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate
25 g (124.8 mmol) of 2-amino-3-benzyloxypyridine were dissolved in 781 ml of ethanol, 102.7 g (624.2 mmol) of ethyl 2-chloroacetoacetate and two table spoons of 4 A molecular sieve were added and the reaction mixture was then heated at reflux (bath temperature 100° C.) for 2 days.
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 gradient-9/1, 4/1).
This gave 20.81 g of the target compound (54percent of theory, purity 99percent).
LC-MS (Method 2): Rt=1.12 min
MS (ESpos): m/z=311 (M+H)+
1H-NMR (400 MHz, DMSO-d6): δ=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).
54% at 100℃; for 48 h; Molecular sieve 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): ?=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).

Reference： [1] Patent: US2014/128386, 2014, A1, . Location in patent: Paragraph 0984; 0985; 0986; 0987; 0988
[2] Patent: US2014/128372, 2014, A1, . Location in patent: Paragraph 0489; 0490; 0491; 0492; 0493
[3] Patent: US2017/57954, 2017, A1, . Location in patent: Paragraph 0620; 0621; 0622; 0623; 0624
[4] Patent: US2016/347770, 2016, A1, . Location in patent: Paragraph 0691; 0692; 0693; 0694; 0695
[5] Journal of Medicinal Chemistry, 1985, vol. 28, # 7, p. 876 - 892
  • 2
  • [ 537-46-2 ]
  • [ 24016-03-3 ]
  • [ 609-15-4 ]
  • [ 96428-50-1 ]
Reference： [1] Patent: US2017/217954, 2017, A1,
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