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

HRID 226397ノート

反応式

HRID 226397 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:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([N:22]2[CH2:26][CH2:25][C@@H:24]([NH2:27])[CH2:23]2)=[O:21])=[CH:18][CH:17]=1.CCN(CC)CC>CN(C=O)C>[Cl:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([N:22]2[CH2:26][CH2:25][C@@H:24]([NH:27][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)[CH2:23]2)=[O:21])=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 68963176(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinamineHCID 86603667Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate

生成物 1

HCID 86603707ethyl (2E)-3-(5-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate収率 63.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (500 mg) in DMF (5 mL) was added (3R)-1-(4-chlorobenzoyl)-3-pyrrolidinamine (951 mg) and Et3N (1.15 mL). After stirring for 3 hours at 120° C., the reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with H2O, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(5-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (601 mg).

後処理

  1. customthe reaction mixture was partitioned between ethyl acetate and H2O
  2. washThe organic layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-f57b190b038a4c4c84adc18698a2f268
出典データセット
uspto-grants-2009_07
特許番号
US07557127B2

反応ノート

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