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Iodine → HCID 178432084, Verbindung

HRID 1037365
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1037365
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[C:22]([NH2:30])[C:23]([NH2:29])=[CH:24][CH:25]=4)[O:20][C:19]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:38][C:39](C)(C)C([O-])([O-])[O-].II>CC#N>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:27](=[O:28])[C:26]4[CH:25]=[CH:24][C:23]5[N:29]=[C:38]([CH3:39])[NH:30][C:22]=5[C:21]=4[O:20][C:19]=3[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 807Iodine2×HCID 21927715Trimethylorthoacetate2×HCID 67067961{1-[4-(7,8-diamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 178432084HCID 178432084, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

To a solution of {1-[4-(7,8-diamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (80 mg, 0.16 mmol) in CH3CN (8 mL) was added trimethylorthoacetate (25 μL, 0.20 mmol) and iodine (4 mg, 0.016 mmol) and the reaction mixture was stirred at RT for 2.5 hours. Further trimethylorthoacetate (50 μL, 0.40 mmol) and iodine (24 mg, 0.096 mmol) were added and the reaction stirred for 1 hour. The reaction was quenched with aqueous Na2S2O3, diluted with ethyl acetate and the phases separated. The organic extracts were washed with brine, dried (NaSO4), filtered and the solvents were removed in vacuo. The resulting residue was subjected to flash chromatography (SiO2, ethyl acetate) to give the title compound as a brown solid (35 mg, 42%). LCMS (Method G): RT=3.18 min, [M+H]+=522.

Aufarbeitung

  1. stirringthe reaction stirred for 1 hour
  2. customThe reaction was quenched with aqueous Na2S2O3
  3. additiondiluted with ethyl acetate
  4. customthe phases separated
  5. washThe organic extracts were washed with brine
  6. dry with materialdried (NaSO4)
  7. filtrationfiltered
  8. customthe solvents were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a8b7a31d68b84dbcbb39c1941961fb54
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546376B2

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