Iodo benzene diacetate → Methyl 2-fluoro-4-[3-(1-quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoate

HRID 1099092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1099092
[F:1][C:2]1[CH:11]=[C:10]([C:12]2[N:17]=[N:16][C:15]([NH:18][NH2:19])=[N:14][CH:13]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N:20]1[C:29]2[C:24](=[CH:25][C:26]([C:30]3([CH:33]=O)[CH2:32][CH2:31]3)=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C.C(O)(=O)C>[F:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:13]=[N:14][C:15]3[N:16]([C:33]([C:30]4([C:26]5[CH:25]=[C:24]6[C:29](=[CH:28][CH:27]=5)[N:20]=[CH:21][CH:22]=[CH:23]6)[CH2:32][CH2:31]4)=[N:19][N:18]=3)[N:17]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

6

Edukt 3

HCID 12217721Iodo benzene diacetateHCID 592162771-Quinolin-6-ylcyclopropanecarbaldehydeHCID 59216321Methyl 2-fluoro-4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate

Produkt 1

HCID 59216283Methyl 2-fluoro-4-[3-(1-quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoateAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-fluoro-4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate (0.17 g, 0.64 mmol) and 1-quinolin-6-ylcyclopropanecarbaldehyde (0.13 g, 0.64 mmol) in ethanol (10 mL) and acetic acid (1 mL) was stirred at RT for 2 h. The mixture was concentrated. The residue was dissolved in methylene chloride (5 mL). To the solution was added iodobenzene diacetate (230 mg, 0.71 mmol) with stirring. The mixture was stirred at RT for 2 h then concentrated. The residue was flash chromatographed on a silica gel column to give the desired product (150 mg). Analytical LCMS: (M+H)+=441.0.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in methylene chloride (5 mL)
  3. stirringwith stirring
  4. stirringThe mixture was stirred at RT for 2 h
  5. concentrationthen concentrated
  6. customchromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-98ff4c7bbd8446119677c84c620e8375
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143251B2

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