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Oxalyl chloride → N-methyl-4-((6-(3-(1-(trifluoromethyl)cyclobutanecarbonyl)ureido)pyridin-3-yl)oxy)picolinamide

HRID 626582
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 626582
[F:1][C:2]([F:11])([F:10])[C:3]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH2:4]1.[C:12](Cl)(=[O:16])C(Cl)=O.[NH2:18][C:19]1[N:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][N:29]=[C:28]([C:32]([NH:34][CH3:35])=[O:33])[CH:27]=2)=[CH:21][CH:20]=1.CC[N:38](C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.O1CCOCC1.CCOC(C)=O.[Ag]OC#N>[CH3:35][NH:34][C:32](=[O:33])[C:28]1[CH:27]=[C:26]([O:25][C:22]2[CH:23]=[N:24][C:19]([NH:18][C:12]([NH:38][C:7]([C:3]3([C:2]([F:1])([F:11])[F:10])[CH2:4][CH2:5][CH2:6]3)=[O:9])=[O:16])=[CH:20][CH:21]=2)[CH:31]=[CH:30][N:29]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27828381-(Trifluoromethyl)cyclobutanecarboxylic acidHCID 904105404-((6-aminopyridin-3-yl)oxy)-N-methylpicolinamide

Produkt 1

HCID 86274905N-methyl-4-((6-(3-(1-(trifluoromethyl)cyclobutanecarbonyl)ureido)pyridin-3-yl)oxy)picolinamideAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 6228DimethylformamideKatalysatorHCID 178513473HCID 178513473, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 1-trifluoromethyl-cyclobutane-1-carboxylic acid (0.413 g, 2.457 mmol) in DCM (8 mL) was treated with oxalyl chloride (0.179 mL, 2.047 mmol) and DMF (1 drop), stirred for at RT for 2 h, treated with silver cyanate (0.982 g, 6.55 mmol), stirred at RT for 1 h, treated with a solution of 4-((6-aminopyridin-3-yl)oxy)-N-methylpicolinamide (0.2 g, 0.819 mmol) and DIEA (0.858 mL, 4.91 mmol) in dioxane (8 mL) and stirred at RT overnight. The mixture was diluted with EtOAc, the solids removed via filtration through diatomaceous earth and washed with EtOAc. The filtrate was washed with satd. NaHCO3, water, then brine and the combined aqueous washes were back-extracted with EtOAc. The combined organics were dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (EtOAc/DCM) to afford N-methyl-4-((6-(3-(1-(trifluoromethyl)cyclobutanecarbonyl)ureido)pyridin-3-yl)oxy)picolinamide (0.259 g, 72%). 1H NMR (400 MHz, DMSO-d6): δ 11.16 (br s, 1H), 10.87 (s, 1H), 8.79 (d, J=5.1 Hz, 1H), 8.53 (d, J=5.6 Hz, 1H), 8.32 (d, J=2.9 Hz, 1H), 8.08 (d, J=9.1 Hz, 1H), 7.81 (dd, J=9.0, 2.9 Hz, 1H), 7.41 (d, J=2.6 Hz, 1H), 7.19 (dd, J=5.6, 2.7 Hz, 1H), 2.78 (d, J=4.8 Hz, 3H), 2.67 (t, J=10.5 Hz, 2H), 2.41 (m, 2H), 1.90-1.87 (m, 2H); MS (ESI) m/z: 438.2 (M+H+).

Aufarbeitung

  1. stirringstirred at RT for 1 h
  2. stirringstirred at RT overnight
  3. customthe solids removed via filtration through diatomaceous earth
  4. washwashed with EtOAc
  5. washThe filtrate was washed with satd
  6. extractionNaHCO3, water, then brine and the combined aqueous washes were back-extracted with EtOAc
  7. dry with materialThe combined organics were dried over Na2SO4
  8. concentrationconcentrated to dryness
  9. custompurified by silica gel chromatography (EtOAc/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-df6594acb818441a9d873ce572bfee4f
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309224B2

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