Diisopropylethylamine → (3S,4S)-benzyl 3-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-4-methylpyrrolidine-1-carboxylate

HRID 877728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877728
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.[NH2:15][C@H:16]1[C@@H:20]([CH3:21])[CH2:19][N:18]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:17]1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:15][C@H:16]3[C@@H:20]([CH3:21])[CH2:19][N:18]([C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])[CH2:17]3)=[C:8]([C:11](=[O:12])[NH2:13])[CH:7]=[N:6][N:5]2[CH:14]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamideHCID 68350278(3S,4S)-benzyl 3-amino-4-methylpyrrolidine-1-carboxylate2×

Produkt 1

HCID 68350361(3S,4S)-benzyl 3-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-4-methylpyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Intermediate 2 (1000 mg, 3.64 mmol), (+/−)-(cis)-benzyl 3-amino-4-methylpyrrolidine-1-carboxylate (Intermediate 5, 1024 mg, 4.37 mmol) and DIPEA (1.27 mL, 7.29 mmol) in DMA (4.0 mL) was heated at 90° C. for 5 h then was allowed to cool to rt and stir overnight. The reaction mixture was added to crushed ice, stirred for 30 min, and the resulting solid that had precipitated was collected by vacuum filtration and was rinsed with water and dried to afford the title compound as a cream colored solid. HPLC (method B) retention time=3.67 min. LCMS (m+1)=472/474 (1:1).

Aufarbeitung

  1. additionThe reaction mixture was added
  2. customto crushed ice
  3. stirringstirred for 30 min
  4. customthe resulting solid that had precipitated
  5. filtrationwas collected by vacuum filtration
  6. washwas rinsed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-03eca52671f74b9abf0af991368a3d33
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987268B2

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