Binap, (A+-)- → 5-((5-Chloro-4-((1-methylpiperidin-4-yl)amino)pyridin-2-yl)amino)pyrazine-2-carbonitrile

HRID 384678노트

반응식

HRID 384678 반응식
[Cl:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.Br[C:18]1[C:23]([C:24]#[N:25])=[N:22][CH:21]=[CH:20][N:19]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>O1CCOCC1>[Cl:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:4][C:5]([NH:8][C:20]2[N:19]=[CH:18][C:23]([C:24]#[N:25])=[N:22][CH:21]=2)=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 596134945-Chloro-N4-(1-methylpiperidin-4-yl)pyridine-2,4-diamineHCID 626739383-Bromopyrazine-2-carbonitrile

생성물 1

HCID 596134475-((5-Chloro-4-((1-methylpiperidin-4-yl)amino)pyridin-2-yl)amino)pyrazine-2-carbonitrile수율 30.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

A solution of 5-chloro-N4-(1-methylpiperidin-4-yl)pyridine-2,4-diamine (0.080 g, 0.33 mmol), 2-bromo-cyanopyrazine (0.040 g, 0.22 mmol), BINAP (0.005 g, 0.02 mmol), sodium tert-butoxide (0.030 g, 0.31 mmol), tris(dibenzylideneacetone)dipalladium chloroform complex (0.009 g, 0.01 mmol) in dioxane (1.6 mL) was stirred at r.t. under nitrogen for 10 min before being heated under microwave irradiation for 30 min at 90° C. The crude reaction mixture was purified by ion exchange on SCX-II acidic resin (1 g) eluting with methanol/dichloromethane (1/1), then 2M ammonia-methanol. The basic fractions were combined and the solvent was removed in vacuo. The crude mixture was purified by preparative thin layer chromatography eluting with methanol/dichloromethane (1/9) to give the title compound as a yellow solid (0.023 g, 30%).

후처리

  1. customThe crude reaction mixture
  2. customwas purified by ion exchange on SCX-II acidic resin (1 g)
  3. washeluting with methanol/dichloromethane (1/1)
  4. customthe solvent was removed in vacuo
  5. customThe crude mixture was purified by preparative thin layer chromatography
  6. washeluting with methanol/dichloromethane (1/9)

출처 및 근거

ORD 기록
ord-58472639952b4bf490ebd769b27ccba5
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367658B2

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