Triethylamine → tert-Butyl 3-((3-amino-6-bromopyrazin-2-ylamino)methyl)piperidine-1-carboxylate

HRID 1478591ノート

反応式

HRID 1478591 の反応式
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.Br[C:17]1[C:18]([NH2:24])=[N:19][CH:20]=[C:21]([Br:23])[N:22]=1.CCN(CC)CC>CS(C)=O>[NH2:24][C:18]1[C:17]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]2)=[N:22][C:21]([Br:23])=[CH:20][N:19]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 27564831-Boc-3-(aminomethyl)piperidine

生成物 1

HCID 86626415tert-Butyl 3-((3-amino-6-bromopyrazin-2-ylamino)methyl)piperidine-1-carboxylate収率 26%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
130 °C

実験手順

tert-butyl 3-(aminomethyl)piperidine-1-carboxylate (4.97 g, 22.40 mmol) was dissolved in DMSO (80 ml), and then 3,5-dibromopyrazine-2-amine (8.5 g, 33.60 mmol) and Et3N (6.3 ml) were added, followed by stirring at 130° C. overnight. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:1), to give tert-butyl 3-(((3-amino-6-bromopyrazine-2-yl)amino)methyl)piperidine-1-carboxylate (2.19 g, two steps: 26%).

後処理

  1. customAfter the completion of the reaction
  2. extractionthe reaction mixture was extracted with H2O, EA, and brine
  3. customby drying
  4. filtration(Na2SO4), filtration, and concentration under reduced pressure
  5. customthe residue was purified by column chromatography (EA:Hex=1:1)

出典と根拠

ORDレコード
ord-f3d96c62a7fc4619acc31183a04d7349
出典データセット
uspto-grants-2016_08
特許番号
US09403831B2

反応ノート

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