4-Methylmorpholine → HCID 67174065, Verbindung

HRID 1256071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256071
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:9][O:8][B:7]([OH:10])[C:6]=2[CH:11]=1.CN1CCOCC1.[C:19]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[S:30](Cl)(=[O:32])=[O:31])#[N:20]>CC#N>[C:19]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[S:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:9][O:8][B:7]([OH:10])[C:6]=2[CH:11]=1)(=[O:32])=[O:31])#[N:20]

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 433636332-Cyano-4-nitrobenzene-1-sulfonyl chloride

Produkt 1

HCID 67174065HCID 67174065, VerbindungAusbeute 27,86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 6-amino-3H-benzo[c][1,2]oxaborol-1-ol (2.98 g, 20 mmol) and NMM in MeCN (150 ml) was added 2-cyano-4-nitrobenzene-1-sulfonyl chloride (5.423 g, 22 mmol) at 0° C., then the solution was stirred at room temperature for overnight. The mixture was concentrated in vacuo at room temperature, and DCM and water was added to the residue. The organic layer was dried over Na2SO4 and concentrated to give the crude product. It was purified by prep. HPLC (column: Luna 300×50.0 mm, 10 u; liquid phase: [A-H2O+0.025% TFA; B-MeCN] B %: 25%-50%, 25 min) to give the title compound (2.0 g, 27.86%) as a yellow solid. 1H NMR: DMSO 400 MHz. δ11.05 (s, 1H), 9.22 (s, 1H), 8.88 (s, 1H), 8.62 (d, J=11.2 Hz, 1H), 8.17 (d, J=8.8 Hz, 1H), 7.45 (s, 1H), 7.31 (d, J=8.0 Hz, 1H), 7.18 (d, J=10.0 Hz, 1H), 4.89 (s, 2H). ESI-MS m/z 360 (M+H, positive); HPLC purity: 93.07% (MaxPlot 190-370 nm), 98.72% (220 nm).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo at room temperature
  2. additionDCM and water was added to the residue
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product
  6. customIt was purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-5ffe9b371bec42e69bf677bc57f90edf
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461134B2

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