C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine → 3-[2-Hydroxy-3-(pyrrolidine-1-carbonyl)phenylamino]-4-{[(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}cyclobut-3-ene-1,2-dione

HRID 1528173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528173
[CH3:1][C:2]1[O:6][C:5]([CH:7]([NH2:13])[C:8]2([CH3:12])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.C([O:16][C:17]1[C:18](=[O:37])[C:19](=O)[C:20]=1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:29])[C:23]=1[OH:35])C>CO>[OH:35][C:23]1[C:24]([C:28]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:29])=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:20]1[C:17](=[O:16])[C:18](=[O:37])[C:19]=1[NH:13][CH:7]([C:5]1[O:6][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:8]1([CH3:12])[CH2:9][O:10][CH2:11]1

Komponenten

4

Edukt 2

HCID 89525357C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamineHCID 895263793-Ethoxy-4-[2-hydroxy-3-(pyrrolidine-1-carbonyl)phenylamino]cyclobut-3-ene-1,2-dione

Produkt 1

HCID 715253443-[2-Hydroxy-3-(pyrrolidine-1-carbonyl)phenylamino]-4-{[(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}cyclobut-3-ene-1,2-dioneAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

385 mg (2.12 mmol) of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine in solution in 3 ml of methanol were added to a solution of 443 mg (1.40 mmol) of 3-ethoxy-4-[2-hydroxy-3-(pyrrolidine-1-carbonyl)phenylamino]cyclobut-3-ene-1,2-dione in 42 ml of methanol. The reaction medium was heated at 50° C. for 13 hours. The reaction medium was concentrated. The residue was taken up with ethyl acetate and was washed twice with a 1 M aqueous sodium dihydrogen phosphate solution. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. 0.62 g of product were obtained in the form of a beige solid. Yield=95%, HPLC=94.06%, Mp=210° C.

Aufarbeitung

  1. concentrationThe reaction medium was concentrated
  2. washwas washed twice with a 1 M aqueous sodium dihydrogen phosphate solution
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-68a87a2bcd7a4b12af8e52c5f430661f
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090596B2

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