Iodine → HCID 24860658, Verbindung

HRID 884782

Reaktionsgleichung

Reaktionsgleichung von HRID 884782
Br[CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[Mg].II.[NH2:11][C:12]1[N:16]([C:17]2[CH:18]=[C:19]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:20]([NH:22][CH:23]2[CH2:25][CH2:24]2)=[O:21])[CH:15]=[N:14][C:13]=1[C:30]#N.C1C[O:35]CC1>>[NH2:11][C:12]1[N:16]([C:17]2[CH:18]=[C:19]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:20]([NH:22][CH:23]2[CH2:25][CH2:24]2)=[O:21])[CH:15]=[N:14][C:13]=1[C:30]([CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1)=[O:35]

Komponenten

6

Edukt 5

HCID 807IodineHCID 8028Tetrahydrofuran3×HCID 5462224MagnesiumHCID 133496544-BromotetrahydropyranHCID 58088961HCID 58088961, Verbindung

Produkt 1

HCID 24860658HCID 24860658, VerbindungAusbeute 30 %

Versuchsvorschrift

A solution of 4-bromo-tetrahydro-pyran (0.82 g, 5 mmol) in dry THF (10 mL) was added dropwise to the suspension of magnesium (132 mg, 5.5 mmol) and iodine (25 mg) in dry THF (20 mL) at 50° C. under N2. The mixture was stirred for 30 min after addition at 50° C., then cooled to room temperature. Then a THF (10 mL) solution of 3-(5-amino-4-cyano-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide (90 mg, 0.32 mmol) was added to the reaction mixture and it was stirred at room temperature for 3 h then quenched with HCl (2N) and stirred at room temperature overnight. The pH of the solution was adjusted pH ˜8 with saturated aqueous K2CO3 was and it was extracted with EtOAc. The organic layer was washed by water and brine, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography on silical gel (EtOAc˜EtOAc:MeOH:Et3N=100:10:1), and the product was obtained as a beige solid (35 mg, 30%). HPLC (4 minute gradient) tR=3.05 min; MS m/z 369.18 [M+H]+.

Aufarbeitung

  1. additionafter addition at 50° C.
  2. stirringwas stirred at room temperature for 3 h
  3. customthen quenched with HCl (2N)
  4. stirringstirred at room temperature overnight
  5. extractionit was extracted with EtOAc
  6. washThe organic layer was washed by water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography on silical gel (EtOAc˜EtOAc:MeOH:Et3N=100:10:1)

Quellen und Nachweise

ORD-Eintrag
ord-e485ab7b3b174dd8b2c99e1dca53aa70
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242117B2

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