Triethylamine → 9-Chloro-3-methyl-5-[1-(3-pyridin-3-yl-propionyl)-piperidin-3-yl]-5H-isoxazolo[4,3-c]quinolin-4-one

HRID 2212194

反応式

HRID 2212194 の反応式
I.[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][CH2:31][C:32](O)=[O:33])[CH:25]=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([C:32](=[O:33])[CH2:31][CH2:30][C:26]4[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=4)[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 181649HOAtHCID 2596243-(Pyridin-3-yl)propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

生成物 1

HCID 219637219-Chloro-3-methyl-5-[1-(3-pyridin-3-yl-propionyl)-piperidin-3-yl]-5H-isoxazolo[4,3-c]quinolin-4-one収率 46.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

Add 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (50 mg, 0.11 mmol), 3-pyridine propionic acid (20 mg, 0.13 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26 mg, 0.13 mmol), 1-hydroxy-7-azabenzotriazole (18 mg, 0.13 mmol), 4-dimethylamino-pyridine (1 mg, 0.01 mmol), and dimethylformamide (3 mL) to a dry roundbottom flask. Stir the reaction under nitrogen, and add triethylamine (30 μL, 0.22 mmol) dropwise. Stir the solution under nitrogen at room temperature overnight. Concentrate the solution and dissolve in 20% isopropanol/chloroform; wash with 1.0N HCl, saturated aqueous sodium bicarbonate solution, and brine; dry over magnesium sulfate; and concentrate. Purify by flash chromatography on silica gel (eluting with 0.5–3.5% methanol/chloroform) to give 22.9 mg of the title compound as a white solid, 45% yield. 1H NMR: consistent with structure. MS (ion spray) 451 (M+).

後処理

  1. customthe reaction under nitrogen
  2. stirringStir the solution under nitrogen at room temperature overnight
  3. concentrationConcentrate the solution
  4. dissolutiondissolve in 20% isopropanol/chloroform
  5. washwash with 1.0N HCl, saturated aqueous sodium bicarbonate solution, and brine
  6. dry with materialdry over magnesium sulfate
  7. concentrationand concentrate
  8. customPurify by flash chromatography on silica gel (eluting with 0.5–3.5% methanol/chloroform)

出典と根拠

ORDレコード
ord-0cf9ab91842045dea587dbe32a54fba3
出典データセット
uspto-grants-2006_09
特許番号
US07101891B2

関連ノート

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