Diisopropylethylamine → Tert-butyl (1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-3-hydroxy-1-oxopropan-2-yl)carbamate

HRID 595437

Reaktionsgleichung

Reaktionsgleichung von HRID 595437
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][OH:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:25]=[C:24]([NH:26][CH:27]([CH3:29])[CH3:28])[C:19]([C:20]([NH:22][NH2:23])=[O:21])=[CH:18][N:17]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:15][C:16]1[CH:25]=[C:24]([NH:26][CH:27]([CH3:29])[CH3:28])[C:19]([C:20]([NH:22][NH:23][C:10](=[O:12])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][OH:14])=[O:21])=[CH:18][N:17]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2949072-((tert-Butoxycarbonyl)amino)-3-hydroxypropanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896896686-Chloro-4-(isopropylamino)nicotinohydrazide

Produkt 1

HCID 131732603Tert-butyl (1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-3-hydroxy-1-oxopropan-2-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoic acid (500 mg, 2.4 mmol) and 6-chloro-4-(isopropylamino)nicotinohydrazide (10) (2.6 mmol, 1.1 equiv.) in DMF (10 mL), DIPEA (12 mmol, 5 equiv.) and HATU (2.6 mmol, 1.1 equiv.) were added and stirred overnight at room temperature. The reaction mass was concentrated under reduced pressure to remove excess of solvent present. Diluted the residue with EtOAc and washed water followed by brine solution. The organic layer was collected, dried over Na2SO4, filtered and concentrated to get tert-butyl (1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-3-hydroxy-1-oxopropan-2-yl)carbamate (53).

Aufarbeitung

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. customto remove excess of solvent present
  3. additionDiluted the residue with EtOAc
  4. washwashed water
  5. customThe organic layer was collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-96f990b7d46e4aa9aea3ec384b5a5167
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242975B2

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