(S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-indazol-6-yl}-amide → (4S)-4-(4-fluorophenyl)-N-[1-(2-hydroxyethyl)-5-methylindazol-6-yl]-2-oxo-3,4-dihydro-1H-pyridine-5-carboxamide

HRID 386666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 386666
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH3:35])=[C:15]([NH:18][C:19]([C:21]3[C@H:26]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[CH2:25][C:24](=[O:34])[NH:23][CH:22]=3)=[O:20])[CH:16]=2)[CH:11]=[N:10]1)(C)(C)C>C(O)(=O)C.O.C1COCC1>[OH:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH3:35])=[C:15]([NH:18][C:19]([C:21]3[C@H:26]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[CH2:25][C:24](=[O:34])[NH:23][CH:22]=3)=[O:20])[CH:16]=2)[CH:11]=[N:10]1

Komponenten

5

Edukt 1

HCID 59377449(S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-indazol-6-yl}-amide

Produkt 1

HCID 59377426(4S)-4-(4-fluorophenyl)-N-[1-(2-hydroxyethyl)-5-methylindazol-6-yl]-2-oxo-3,4-dihydro-1H-pyridine-5-carboxamideAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-indazol-6-yl}-amide (46 mg, 0.09 mmol) was dissolved in 3 ml of a 3:1:1 mixture of acetic acid, water and THF. The mixture was allowed to stir overnight at room temperature. The solution was concentrated in vacuo, and the residue was purified by flash chromatography (95:5 dichloromethane/methanol) to give 24 mg (70.6%) of (S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid [1-(2-hydroxy-ethyl)-5-methyl-1H-indazol-6-yl]-amide white crystalline solid; MS (ES+) m/z 409 (M+H).

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (95:5 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-048c777770ca4d15b134dd81ecb0c5f4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372865B2

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