Triethylamine → 1-(3-Fluoro-4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}benzoyl)azetidin-3-ol

HRID 909502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909502
[F:1][C:2]1[CH:30]=[C:29]([C:31]([N:33]2[CH2:36][CH:35]([O:37]C3CCCCO3)[CH2:34]2)=[O:32])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([C:17]2[NH:21][C:20]([C:22]3[S:23][CH:24]=[CH:25][N:26]=3)=[CH:19][CH:18]=2)[CH:8]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][O:14][CH3:15])[CH:10]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(N(CC)CC)C>CO>[F:1][C:2]1[CH:30]=[C:29]([CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([C:17]2[NH:21][C:20]([C:22]3[S:23][CH:24]=[CH:25][N:26]=3)=[CH:19][CH:18]=2)[CH:8]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][O:14][CH3:15])[CH:10]=1)[C:31]([N:33]1[CH2:34][CH:35]([OH:37])[CH2:36]1)=[O:32]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 666808962-(5-{3-(2-Fluoro-4-{[3-(tetrahydro-2H-pyran-2-yloxy)azetidin-1-yl]carbonyl}phenoxy)-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrol-2-yl)-1,3-thiazole

Produkt 1

HCID 580655011-(3-Fluoro-4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}benzoyl)azetidin-3-olAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2-(5-{3-(2-Fluoro-4-{[3-(tetrahydro-2H-pyran-2-yloxy)azetidin-1-yl]carbonyl}phenoxy)-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrol-2-yl)-1,3-thiazole (110 mg, 0.181 mmol) synthesized in Example (42b) was dissolved in methanol (10 mL), and 10-camphorsulfonic acid (20 mg, 0.086 mmol) was added, followed by stirring at room temperature overnight under nitrogen atmosphere. To the reaction solution, triethylamine (0.1 mL) was added, and the solvent was distilled off under reduced pressure. The resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=90%-100%) to afford the desired compound (62 mg, yield 65%) as a yellow solid.

Aufarbeitung

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe resulting residue was purified
  3. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=90%-100%)

Quellen und Nachweise

ORD-Eintrag
ord-3884d3c8f6bf497882bdb5f071edf59d
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017610B2

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