Triethylamine → ethyl (2E)-3-(5-{[(3R)-1-(4-fluorobenzyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate

HRID 2376077ノート

反応式

HRID 2376077 の反応式
Cl[C:2]1[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1.Cl.Cl.[F:17][C:18]1[CH:30]=[CH:29][C:21]([CH2:22][N:23]2[CH2:27][CH2:26][C@@H:25]([NH2:28])[CH2:24]2)=[CH:20][CH:19]=1.C(N(CC)CC)C>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][N:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:2]3[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=3)[CH2:24]2)=[CH:29][CH:30]=1

参加物

4

反応物 3

HCID 8471TriethylamineHCID 53256257HCID 53256257、化合物HCID 86603667Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate

生成物 1

HCID 86603699ethyl (2E)-3-(5-{[(3R)-1-(4-fluorobenzyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate収率 47%

反応条件

温度
100 °C

実験手順

A mixture of ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (300 mg, 1.41 mmol), (3R)-1-(4-fluorobenzyl)-3-pyrrolidinamine dihydrochloride (565 mg, 2.11 mmol) and triethylamine (928 mg, 9.17 mmol) was stirred at 100° C. for 6 hrs. The reaction mixture was evaporated in vacuo and the residue was partitioned between water and EtOAc. The organic layer was separated, washed water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (35% EtOAc/hexane-50% EtOAc/hexane) to give ethyl (2E)-3-(5-{[(3R)-1-(4-fluorobenzyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (245 mg, 47%) as an oil.

後処理

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was partitioned between water and EtOAc
  3. customThe organic layer was separated
  4. washwashed water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (35% EtOAc/hexane-50% EtOAc/hexane)

出典と根拠

ORDレコード
ord-d10ff6ecd432479a91bf9f18b51e2f56
出典データセット
uspto-grants-2008_12
特許番号
US07465731B2

反応ノート

読み込み中…