Methyl iodide → Tert-butyl 4-methoxy-4-((2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)methyl)piperidine-1-carboxylate

HRID 2035674ノート

反応式

HRID 2035674 の反応式
[OH:1][C:2]1([CH2:15][O:16][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[N:25]=[C:24]([C:27]2[N:31]4[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:30]4=[N:29][N:28]=2)[CH:23]=[CH:22]3)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].I[CH3:40]>CN(C)C=O>[CH3:40][O:1][C:2]1([CH2:15][O:16][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[N:25]=[C:24]([C:27]2[N:31]4[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:30]4=[N:29][N:28]=2)[CH:23]=[CH:22]3)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:4][CH2:3]1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67234438Tert-butyl 4-hydroxy-4-((2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)methyl)piperidine-1-carboxylate

生成物 1

HCID 67234513Tert-butyl 4-methoxy-4-((2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)methyl)piperidine-1-carboxylate収率 49.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of tert-butyl 4-hydroxy-4-((2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)methyl)piperidine-1-carboxylate (50 mg, 0.10 mmol) and sodium hydride (18 mg, 0.82 mmol) in dimethylformamide (1 mL) was stirred at ambient temperature for 15 minutes. Iodomethane (0.051 mL, 0.82 mmol) was added and the solution was stirred at ambient temperature overnight. The reaction was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed twice with saturated aqueous ammonium carbonate. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was triturated with hexanes and further purified by preparative thin layer chromatography with 1:9 methanol/dichloromethane to provide 25 mg (46%) of desired product.

後処理

  1. stirringthe solution was stirred at ambient temperature overnight
  2. concentrationThe reaction was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed twice with saturated aqueous ammonium carbonate
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with hexanes
  9. customfurther purified by preparative thin layer chromatography with 1:9 methanol/dichloromethane

出典と根拠

ORDレコード
ord-bd57e83d58bd4aef9c5ce0e07460c242
出典データセット
uspto-grants-2013_11
特許番号
US08575145B2

反応ノート

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