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

HRID 595466노트

반응식

HRID 595466 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63740e569a1d4ba3a23f257698506b91
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242976B2

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