Ethyl Acetate → 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

HRID 1753725

Reaktionsgleichung

Reaktionsgleichung von HRID 1753725
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 866575662-{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

Produkt 1

HCID 866575652-[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

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-835b4f7e3b6c43f2a48981b31b7ee73f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09167821B2

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