Diisopropylethylamine → Cannabinoid receptor-2 agonists

HRID 336184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336184
Cl.[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12]([C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]2)=[O:13])[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[O:20]=[S:21]1(=[O:30])[CH2:26][CH2:25][N:24]([C:27](Cl)=[O:28])[CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C>C1COCC1>[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12]([C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][N:15]2[C:27]([N:24]2[CH2:25][CH2:26][S:21](=[O:30])(=[O:20])[CH2:22][CH2:23]2)=[O:28])=[O:13])[CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 216949071,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl chlorideHCID 86660400(S)-Piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl) amide hydrochloride

Produkt 1

HCID 70865101Cannabinoid receptor-2 agonists

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of (S)-Piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl) amide hydrochloride (150 mg; 0.521 mmol) in THF (6 mL) is added 1,1-Dioxo-1λ6-thiomorpholine-4-carbonyl chloride (102.97 mg; 0.521 mmol) and N,N-diisopropylethylamine (0.186 mL; 1.07 mmol). The reaction mixture is stirred at room temperature for 4 hours. The reaction mixture is quenched with water and extracted with methylene chloride twice. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using methanol/methylene chloride provides the title compound, m/z 413 [M+H+].

Aufarbeitung

  1. customThe reaction mixture is quenched with water
  2. extractionextracted with methylene chloride twice
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3a5694dcd6064dd19eb23cbf73c14f35
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889670B2

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