4-Methylmorpholine → N-[5-Bromo-2-chloro-4-(ethylamino)-3-pyridinyl]-2-cyanoacetamide

HRID 1863996ノート

反応式

HRID 1863996 の反応式
[Br:1][C:2]1[C:3]([NH:10][CH2:11][CH3:12])=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.Cl.CN(C)CCCN=C=NCC.[C:25]([CH2:27][C:28](O)=[O:29])#[N:26].CN1CCOCC1>C(Cl)Cl>[Br:1][C:2]1[C:3]([NH:10][CH2:11][CH3:12])=[C:4]([NH:9][C:28](=[O:29])[CH2:27][C:25]#[N:26])[C:5]([Cl:8])=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 9740Cyanoacetic acid2 回HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2 回HCID 45480182HCID 45480182、化合物

生成物 1

HCID 57973904N-[5-Bromo-2-chloro-4-(ethylamino)-3-pyridinyl]-2-cyanoacetamide収率 76.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-bromo-2-chloro-N4-ethyl-pyridine-3,4-diamine (II, 550 g, 2.21 mol) in CH2Cl2 (5.5 L) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (634.5 g, 3.31 mol), cyanoacetic acid (282 g, 3.31 mol) and N-methylmorpholine (897 g, 8.84 mol). A significant exotherm (˜20° C.) was observed upon the addition of the 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and cyanoacetic acid. After stirring at ambient temperature for 2 h, the solvent was removed under reduced pressure. The resulting reside was extracted with warm EtOAc (40° C., 20 L) and water (40° C., 8 L). The aqueous layer was washed with addition EtOAc (10 L) and the combined organic extracts were washed with water (10 L). The organic extract was concentrated under reduced pressure to a slurry and filtered. The solid was washed with EtOAc and dried to give 534 g (76% yield) of the desired compound (III) as a white crystalline solid. This was used in the next step without further purification. MS (ES+) m/z 317 (M+H)+.

後処理

  1. customthe solvent was removed under reduced pressure
  2. extractionThe resulting reside was extracted with warm EtOAc (40° C., 20 L) and water (40° C., 8 L)
  3. washThe aqueous layer was washed with addition EtOAc (10 L)
  4. washthe combined organic extracts were washed with water (10 L)
  5. extractionThe organic extract
  6. concentrationwas concentrated under reduced pressure to a slurry
  7. filtrationfiltered
  8. washThe solid was washed with EtOAc
  9. customdried

出典と根拠

ORDレコード
ord-2f806903e570408b82673e6dda5e823d
出典データセット
uspto-grants-2009_12
特許番号
US07625890B2

反応ノート

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