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Water → (RS)-1-[2-(5,6-Difluoro-1-methyl-1H-benzoimidazol-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone

HRID 1367025
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1367025
[F:1][C:2]1[C:32]([F:33])=[CH:31][C:5]2[NH:6][C:7]([CH2:9][CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][N:11]3[C:16]([C:18]3[N:19]=[C:20]([CH3:30])[S:21][C:22]=3[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[O:17])=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].I[CH3:37].O>CN(C=O)C.Cl>[F:1][C:2]1[C:32]([F:33])=[CH:31][C:5]2[N:6]([CH3:37])[C:7]([CH2:9][CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][N:11]3[C:16]([C:18]3[N:19]=[C:20]([CH3:30])[S:21][C:22]=3[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[O:17])=[N:8][C:4]=2[CH:3]=1
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Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 17973672(RS)-1-[2-(5,6-Difluoro-1H-benzoimidazol-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone

Produkt 1

HCID 17973693(RS)-1-[2-(5,6-Difluoro-1-methyl-1H-benzoimidazol-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone
Ausbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(RS)-1-[2-(5,6-Difluoro-1H-benzoimidazol-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone, E35 (400 mg, 0.85 mmol) was slowly added to an ice-cooled slurry of NaH (68 mg, 60% dispersion on mineral oil, 1.7 mmol) in DMF (10 ml). After 0.5 h iodomethane (0.90 mmol) was added. The reaction mixture was stirred at room temperature, under argon for 16 h. 2N HCl (9 drops) then water (100 ml) were added. The aqueous phase was extracted with EtOAc (2×) and the combined organics washed with brine, dried (Na2SO4) and the solvent removed in vacuo. The residue was chromatographed (silica gel, 50-100% pentane-ethyl acetate). Residual DMF was removed by dissolving in ethyl acetate/diethyl ether and washing with water (2×). Drying (Na2SO4) and removal of the solvent in vacuo afforded the title compound as a pale yellow solid (142 mg, 34%).

Aufarbeitung

  1. extractionThe aqueous phase was extracted with EtOAc (2×)
  2. washthe combined organics washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was chromatographed (silica gel, 50-100% pentane-ethyl acetate)
  6. customResidual DMF was removed
  7. dissolutionby dissolving in ethyl acetate/diethyl ether
  8. washwashing with water (2×)
  9. customDrying
  10. custom(Na2SO4) and removal of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-32f5c92a886444bdb2032aa194930dcf
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07893090B2

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