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

HRID 384685

반응식

HRID 384685 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fe836271d6be49e88f25319711a41df2
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367658B2

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