Triethylamine → Methyl 2-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-2-oxoacetate

HRID 877533

反応式

HRID 877533 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][N:3]=1.CCN(CC)CC.Cl[C:24](=[O:29])[C:25]([O:27][CH3:28])=[O:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:5]([C:6]([NH:8][NH:9][C:24](=[O:29])[C:25]([O:27][CH3:28])=[O:26])=[O:7])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 896896686-Chloro-4-(isopropylamino)nicotinohydrazide

生成物 1

HCID 89689816Methyl 2-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-2-oxoacetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 6-chloro-4-(isopropylamino)nicotinohydrazide (10) (200 mg, 0.35 mmol) in DCM (10 mL), Et3N (3.1 mmol, 3 equiv) was added and cooled to 0° C. Methyl 2-chloro-2-oxoacetate (0.42 mmol, 1.2 equiv) was added dropwise and stirred for 6 h at room temperature. The reaction mixture was quenched with aq. NaHCO3 solution and extracted in DCM. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography through silica gel and MeOH: DCM as eluent to afford methyl 2-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-2-oxoacetate.

後処理

  1. customThe reaction mixture was quenched with aq. NaHCO3 solution
  2. extractionextracted in DCM
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography through silica gel and MeOH

出典と根拠

ORDレコード
ord-45185bd5531d4c0094c07877bc2ded5b
出典データセット
uspto-grants-2015_03
特許番号
US08987311B2

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