Acetic Acid → 1-methyl-1-[(E)-1-[3-(1-quinolin-6-ylcyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]urea

HRID 456117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456117
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([C:14]4[N:18]5[N:19]=[C:20]([C:23](=O)[CH3:24])[CH:21]=[CH:22][C:17]5=[N:16][N:15]=4)[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[CH3:30][N:31]([C:33]([NH2:35])=[O:34])[NH2:32]>CO>[CH3:30][N:31]([C:33]([NH2:35])=[O:34])/[N:32]=[C:23](/[C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:14]([C:11]3([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:1]=[CH:2][CH:3]=[CH:4]5)[CH2:12][CH2:13]3)=[N:15][N:16]=2)[N:19]=1)\[CH3:24]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 2560041-Amino-1-methylureaHCID 581905101-(3-(1-(Quinolin-6-yl)cyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Produkt 1

HCID 509161621-methyl-1-[(E)-1-[3-(1-quinolin-6-ylcyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]ureaAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1-[3-(1-quinolin-6-yl-cyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-ethanone (30 mg, 0.091 mmol), acetic acid (0.1 mL) and 1-methylhydrazinecarboxamide (16.2 mg, 0.18 mmol) in methanol (5 mL) was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was diluted with DCM, washed with sat. aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography in silica gel eluting with a CH2Cl2/MeOH gradient to afford the title compound (14.9 mg, 41%) as yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.84 (dd, 1H), 8.30 (d, 1H), 8.22 (d, 1H), 8.13 (d, 1H), 7.94-7.92 (m, 2H), 7.70 (dd, 1H), 7.49 (dd, 1H), 6.64 (s, 2H), 3.21 (s, 3H), 2.16 (s, 3H), 1.78-1.75 (m, 2H), 1.68-1.65 (m, 2H). LCMS (method A): [MH]+=401, tR=4.11 min.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with DCM
  3. washwashed with sat. aqueous NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography in silica gel eluting with a CH2Cl2/MeOH gradient

Quellen und Nachweise

ORD-Eintrag
ord-a4f0b75ad9d94535950e3253af9b7e60
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497368B2

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