Hydrochloric Acid → (R)-N-Hydroxy-4-{4-[4-(4-hydroxymethyl-piperidin-1-yl)-phenyl]-2-oxo-2H-pyridin-1-yl}-2-methanesulfonyl-2-methyl-butyramide hydrochloride

HRID 1475899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1475899
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][N:18]([CH2:21][CH2:22][C@:23]([S:35]([CH3:38])(=[O:37])=[O:36])([CH3:34])[C:24]([NH:26][O:27]C4CCCCO4)=[O:25])[C:17](=[O:39])[CH:16]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[ClH:40].O1CCOCC1>C(Cl)Cl.CO>[ClH:40].[OH:27][NH:26][C:24](=[O:25])[C@@:23]([S:35]([CH3:38])(=[O:37])=[O:36])([CH3:34])[CH2:22][CH2:21][N:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:11]=[CH:10][C:9]([N:6]3[CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4][CH2:5]3)=[CH:14][CH:13]=2)=[CH:16][C:17]1=[O:39]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86671966HCID 86671966, Verbindung

Produkt 1

HCID 86671964(R)-N-Hydroxy-4-{4-[4-(4-hydroxymethyl-piperidin-1-yl)-phenyl]-2-oxo-2H-pyridin-1-yl}-2-methanesulfonyl-2-methyl-butyramide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(R)-4-{4-[4-(4-hydroxymethyl-piperidin-1-yl)-phenyl]-2-oxo-2H-pyridin-1-yl}-2-methanesulfonyl-2-methyl-N-(tetrahydro-pyran-2-yloxy)-butyramide (85.1 mg, 0.152 mmol) was dissolved in methylene chloride (5 mL) at ambient temperature. To this solution was added 4M HCl in 1,4-dioxane (0.304 mL, 1.22 mmol) and methanol (1 ml). The resulting solution was stirred at ambient temperature for 45 minutes. The solution was concentrated to a crude residue in vacuo. To the residue was added ethyl acetate (10 ml) and the resulting slurry was stirred overnight at ambient temperature. The slurry was filtered and washed with ethyl acetate/heptanes (1:1). The solid was dried in vacuo to afford (R)—N-Hydroxy-4-{4-[4-(4-hydroxymethyl-piperidin-1-yl)-phenyl]-2-oxo-2H-pyridin-1-yl}-2-methanesulfonyl-2-methyl-butyramide hydrochloride as an off-white solid. (72.7 mg). LCMS: M+1 478.6. 1H NMR (CD3OD, 400 MHZ) dppm, 7.82 (2H, d), 7.79 (1H, d), 6.84 (1H, d), 6.80-6.77 (1H, dd), 4.35-4.28 (1H, m), 4.00-3.93 (1H, m), 3.79-3.72 (4H, m), 3.55 (2H, d), 3.09 (3H, s), 2.64-2.56 (1H, m), 2.40-2.33 (1H, m), 2.16-2.13 (2H, d), 2.00-1.92 (1H, m), 1.87-1.76 (2H, m), 1.70 (3H, s).

Aufarbeitung

  1. concentrationThe solution was concentrated to a crude residue in vacuo
  2. additionTo the residue was added ethyl acetate (10 ml)
  3. stirringthe resulting slurry was stirred overnight at ambient temperature
  4. filtrationThe slurry was filtered
  5. washwashed with ethyl acetate/heptanes (1:1)
  6. customThe solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3cf1d0e4d3914138900c71e852df9e36
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018384B2

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