Triethylamine → 9-Chloro-3-methyl-5-[1-(3-pyridin-2-yl-propionyl)-piperidin-3-yl]-5H-isoxazolo[4,3-c]quinolin-4-one

HRID 2212195

반응식

HRID 2212195 반응식
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]=[CH:26][C:25]=1[CH2:30][CH2:31][C:32](O)=[O:33].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:25]4[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=4)[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 181649HOAtHCID 5642923-(Pyridin-2-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

생성물 1

HCID 219637209-Chloro-3-methyl-5-[1-(3-pyridin-2-yl-propionyl)-piperidin-3-yl]-5H-isoxazolo[4,3-c]quinolin-4-one수율 77.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

Add 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (50 mg, 0.11 mmol), 2-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 saturated aqueous sodium bicarbonate solution and brine; dry over magnesium sulfate; and concentrate. Purify by flash chromatography on silica gel (eluting with 0–2% methanol/chloroform) to give 38.5 mg of the title compound as a white solid, 76% yield. 1H NMR: consistent with structure. MS (ion spray) 451 (M+).

후처리

  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 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 0–2% methanol/chloroform)

출처 및 근거

ORD 기록
ord-1d0529684373416cb15e36ac09d2a65f
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101891B2

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