2-Amino-5-fluoropyridine → rac-cis-(2-(((5-Fluoropyridin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

HRID 60846

Reaktionsgleichung

Reaktionsgleichung von HRID 60846
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][C@H:18]([CH3:22])[C@@H:17]2[CH:23]=O)=[O:15])=[CH:4][CH:3]=1.[F:25][C:26]1[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][CH2:23][C@H:17]2[C@@H:18]([CH3:22])[CH2:19][CH2:20][CH2:21][N:16]2[C:14]([C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:15])=[N:30][CH:31]=1

Komponenten

7

Edukt 3

HCID 27377012-Amino-5-fluoropyridineHCID 5003444Sodium cyanoborohydrideHCID 131737135rac-cis-1-(5-(4-Fluorophenyl)-2-methylthiazole-4-carbonyl)-3-methylpiperidine-2-carbaldehyde

Produkt 1

HCID 131737136rac-cis-(2-(((5-Fluoropyridin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittelHCID 10129899Acetic acid methanolLösungsmittel

Versuchsvorschrift

To a stirred solution of rac-cis-1-(5-(4-fluorophenyl)-2-methylthiazole-4-carbonyl)-3-methylpiperidine-2-carbaldehyde and 5-fluoropyridin-2-amine in methanol/acetic acid (50:1) was added sodium cyanoborohydride at 0° C. The reaction was then stirred at rt overnight. After ˜16 h, the reaction mixture was transferred to a seperatory funnel, diluted with EtOAc, saturated NaHCO3 and the layers separated. The organic layer was washed with water, brine, dried (MgSO4), and concentrated in vacuo. The crude reaction mixture was purified by reverse-phase preparative HPLC to afford the title compound. MS (ESI) 443.2 (M+H).

Aufarbeitung

  1. waitAfter ˜16 h
  2. customthe reaction mixture was transferred to a seperatory funnel
  3. customthe layers separated
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. customwas purified by reverse-phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-dbdb52e682a049b0969c0e448bb73064
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440982B2

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