Diisopropylethylamine → Tert-butyl 4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl]carbonyl)-1,4-diazepane-1-carboxylate

HRID 1402755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402755
[NH:1]1[CH2:4][CH:3]([C:5]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]2)=[O:6])[CH2:2]1.CCN(C(C)C)C(C)C.[CH3:30][C:31]1[N:36]=[CH:35][C:34]([C:37](Cl)=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:30][C:31]1[N:36]=[CH:35][C:34]([C:37]([N:1]2[CH2:4][CH:3]([C:5]([N:7]3[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]3)=[O:6])[CH2:2]2)=[O:38])=[CH:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 218904586-Methylnicotinoyl chlorideHCID 66739652Tert-butyl 4-(azetidin-3-ylcarbonyl)-1,4-diazepane-1-carboxylate

Produkt 1

HCID 66739625Tert-butyl 4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl]carbonyl)-1,4-diazepane-1-carboxylateAusbeute 36,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a stirred solution of tert-butyl 4-(azetidin-3-ylcarbonyl)-1,4-diazepane-1-carboxylate (1.02 g, 3.6 mmol) and DIPEA (1.41 g, 10.8 mmol) in DCM (20 mL) was added a solution of 6-methylpyridine-3-carbonyl chloride (420 mg, 4.32 mmol) in DCM (5 mL) at 0° C. After 3 hours the reaction was diluted with DCM (10 mL), washed with saturated aqueous NaHCO3 (10 mL), brine (5 mL), dried (MgSO4), filtered and concentrated at reduced pressure. Purification by silica FCC (eluting with 100:0:0 to 95:4.5:0.5 gradient of DCM/MeOH/NH3) gave the title compound (527 mg, 36%) as an orange-brown oil.

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3 (10 mL), brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customPurification
  6. washby silica FCC (eluting with 100:0:0 to 95:4.5:0.5 gradient of DCM/MeOH/NH3)

Quellen und Nachweise

ORD-Eintrag
ord-0d8891ce1c9244c98d578357879f29ec
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912176B2

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