Triethylamine → N-(5-Bromo-4-(1-methylpiperidin-4-ylamino)pyridin-2-yl)pivalamide

HRID 384685

Reaktionsgleichung

Reaktionsgleichung von HRID 384685
[Br:1][C:2]1[C:3](Cl)=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23](OCC2C=CC=CC=2)=O)[CH2:19][CH2:18]1.C(N(CC)CC)C>CN1C(=O)CCC1.CO>[Br:1][C:2]1[C:3]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 178466404-Amino-1-N-Cbz-piperidineHCID 59613421N-(5-bromo-4-chloropyridin-2-yl)-2,2-dimethylpropanamide

Produkt 1

HCID 59613507N-(5-Bromo-4-(1-methylpiperidin-4-ylamino)pyridin-2-yl)pivalamideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

N-(5-Bromo-4-chloropyridin-2-yl)pivalamide (Synthesis 155-A) (1.08 g, 3.70 mmol), benzyl 4-aminopiperidine-1-carboxylate (1.736 g, 7.41 mmol), and triethylamine (1.041 mL, 7.41 mmol) in NMP (7.41 mL) in a sealed vial was heated to 210° C. by microwave irradiation for 1.5 hr. The cooled solution was diluted with MeOH and purified by ion exchange on Isolute SCX II acidic resin eluting with MeOH then 2M NH3 in MeOH. He basic fractions were combined and volatiles were removed in vacuo. The crude product was dissolved in dichloromethane and loaded onto a Biotage silica column. Flash column chromatography eluting with a gradient of EtOAc in hexanes gave N-(5-bromo-4-(1-methylpiperidin-4-ylamino)pyridin-2-yl)pivalamide (0.536 g, 1.095 mmol, 30%) as a clear glass.

Aufarbeitung

  1. custompurified by ion exchange on Isolute SCX II acidic resin
  2. washeluting with MeOH
  3. customvolatiles were removed in vacuo
  4. dissolutionThe crude product was dissolved in dichloromethane
  5. washFlash column chromatography eluting with a gradient of EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-fe836271d6be49e88f25319711a41df2
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367658B2

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