Acetic Anhydride → N-[[2-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-5-(2,6-dimethyl-4-pyridinyl)-4-thiazolyl]methyl]-acetamide

HRID 473982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473982
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[S:10][C:11]([C:16]3[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([CH3:23])[CH:17]=3)=[C:12](NC)[N:13]=2)[CH2:3]1.[CH2:24]([N:26]([CH2:29]C)CC)[CH3:25].C(OC(=O)C)(=[O:33])C>ClCCl>[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]2[S:10][C:11]([C:16]3[CH:17]=[C:18]([CH3:23])[N:19]=[C:20]([CH3:22])[CH:21]=3)=[C:12]([CH2:29][NH:26][C:24](=[O:33])[CH3:25])[N:13]=2)[CH2:5]1

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67216071[2-(cis-2,6-Dimethyl-morpholin-4-yl)-5-(2,6-dimethyl-pyridin-4-yl)-thiazol-4-yl]-methylamine

Produkt 1

HCID 53237123N-[[2-[(2R,6S)-2,6-dimethyl-4-morpholinyl]-5-(2,6-dimethyl-4-pyridinyl)-4-thiazolyl]methyl]-acetamideAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of Intermediate 5 (150 mg, 0.45 mmol) and triethylamine (0.063 mL, 0.54 mmol) was stirred in dichloromethane (6 mL) at room temperature. Acetic acid anhydride (0.051 mL, 0.54 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was washed with a potassium carbonate solution. The organic layer was dried on MgSO4, filtered, and evaporated. The residue was purified by preparative HPLC (RP Shandon Hyperprep C18 BDS—8 μm, 250 g, 5 cm; mobile phase (0.25% NH4HCO3 solution in water, MeOH+CH3CN)), yielding 100 mg (59%) of Compound 60.

Aufarbeitung

  1. washThe reaction mixture was washed with a potassium carbonate solution
  2. customThe organic layer was dried on MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by preparative HPLC (RP Shandon Hyperprep C18 BDS—8 μm, 250 g, 5 cm; mobile phase (0.25% NH4HCO3 solution in water, MeOH+CH3CN))

Quellen und Nachweise

ORD-Eintrag
ord-4435f6b8aee34d05a7423ccff5df4417
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637510B2

Notizen zur Reaktion

Wird geladen…