Acetaldehyde → 6-{6-[2-(1-ethylpiperidin-4-yl)ethoxy]-5-(trifluoromethyl)pyridin-3-yl}-9-methyl-9H-purine-2-carbonitrile

HRID 522303ノート

反応式

HRID 522303 の反応式
Cl.[CH3:2][N:3]1[CH:11]=[N:10][C:9]2[C:4]1=[N:5][C:6]([C:31]#[N:32])=[N:7][C:8]=2[C:12]1[CH:13]=[N:14][C:15]([O:22][CH2:23][CH2:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:34].[Na+].C(=O)C.C([O-])(O)=O.[Na+]>ClC(Cl)C.C(Cl)(Cl)Cl.C(O)(=O)C.C(N(CC)CC)C>[CH2:33]([N:28]1[CH2:29][CH2:30][CH:25]([CH2:24][CH2:23][O:22][C:15]2[N:14]=[CH:13][C:12]([C:8]3[N:7]=[C:6]([C:31]#[N:32])[N:5]=[C:4]4[C:9]=3[N:10]=[CH:11][N:3]4[CH3:2])=[CH:17][C:16]=2[C:18]([F:21])([F:19])[F:20])[CH2:26][CH2:27]1)[CH3:34]

参加物

9

反応物 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 1178996109-methyl-6-{6-[2-(piperidin-4-yl)ethoxy]-5-(trifluoromethyl)pyridin-3-yl}-9H-purine-2-carbonitrile monohydrochloride

生成物 1

HCID 717616296-{6-[2-(1-ethylpiperidin-4-yl)ethoxy]-5-(trifluoromethyl)pyridin-3-yl}-9-methyl-9H-purine-2-carbonitrile収率 61.1%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒HCID 63651,1-Dichloroethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

Triethylamine (2.7 mL) was added to a suspension of 9-methyl-6-{6-[2-(piperidin-4-yl)ethoxy]-5-(trifluoromethyl)pyridin-3-yl}-9H-purine-2-carbonitrile monohydrochloride (3.0 g) in dichloroethane (60 mL) at room temperature, and the mixture was stirred at the same temperature for 20 minutes. After the reaction mixture was ice-cooled, acetic acid (1.8 mL), sodium triacetoxyborohydride (2.7 g) were added thereto, and a solution of acetaldehyde (1.1 mL) in dichloroethane (5 mL) was added thereto. The mixture was stirred for 1 hour under ice-cooling. After a saturated aqueous NaHCO3 solution was added to the reaction mixture, extraction thereof was performed using CHCl3, and the extract was washed with saturated brine. The organic layer was dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was suspended in EtOH (80 mL), and the suspension was dissolved by stirring for 30 minutes while heating to reflux. The mixture was cooled to room temperature, and the precipitate was collected by filtration, whereby 6-{6-[2-(1-ethylpiperidin-4-yl)ethoxy]-5-(trifluoromethyl)pyridin-3-yl}-9-methyl-9H-purine-2-carbonitrile (1.8 g) was obtained as a crystal (heat absorption peak temperature obtained by a TG/DTA analysis: near 191° C.).

後処理

  1. temperaturecooled
  2. stirringThe mixture was stirred for 1 hour under ice-
  3. temperaturecooling
  4. washthe extract was washed with saturated brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionthe suspension was dissolved
  9. stirringby stirring for 30 minutes
  10. temperaturewhile heating to reflux
  11. filtrationthe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-40e682a8485a413f93e5d28d7f3afd1e
出典データセット
uspto-grants-2016_05
特許番号
US09328118B2

反応ノート

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