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

HRID 384685

反応式

HRID 384685 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fe836271d6be49e88f25319711a41df2
出典データセット
uspto-grants-2013_02
特許番号
US08367658B2

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