Ethyl Acetate → HCID 86657565, Verbindung

HRID 38722

Reaktionsgleichung

Reaktionsgleichung von HRID 38722
C(N[C:5]1[CH:10]=[CH:9][C:8](S(N=[N+]=[N-])(=O)=O)=[CH:7][CH:6]=1)(=O)C.O=[C:18](C)[CH2:19]P(=O)(OC)OC.[F:27][CH:28]([F:64])[C:29]1[CH:33]=[C:32]([CH:34]([F:36])[F:35])[N:31]([CH2:37][C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]3[S:47][CH:48]=[C:49]([C:51]4[CH2:55][CH:54](C5C=CC=CC=5C=O)[O:53][N:52]=4)[N:50]=3)[CH2:42][CH2:41]2)=[O:39])[N:30]=1.C(OCC)(=O)C>C(#N)C.CO.O>[F:64][CH:28]([F:27])[C:29]1[CH:33]=[C:32]([CH:34]([F:36])[F:35])[N:31]([CH2:37][C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]3[S:47][CH:48]=[C:49]([C:51]4[CH2:55][CH:54]([C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=5[C:18]#[CH:19])[O:53][N:52]=4)[N:50]=3)[CH2:42][CH2:41]2)=[O:39])[N:30]=1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 51291854-Acetamidobenzenesulfonyl azideHCID 86657566HCID 86657566, Verbindung

Produkt 1

HCID 86657565HCID 86657565, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 4-acetamidobenzenesulphonyl azide (140 mg) in acetonitrile (10 ml) was added, at room temperature, dimethyl 2-oxopropylphosphonate (97 mg). After stirring for 2 hours, 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}benzaldehyde (267 mg) in methanol (2 ml) was added to the reaction mixture. After stirring for 8 hours, the reaction mixture was admixed with ethyl acetate and water and extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[5-(2-ethynylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (50 mg).

Aufarbeitung

  1. stirringAfter stirring for 8 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-46d18b2aeb4b45df8b337b9f435ebe4d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524743B2

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