1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (3-Chloro-2-cyclopropylamino-4,5-difluorobenzoyl)-hydrazinecarboxylic acid tert-butyl ester

HRID 10305

反応式

HRID 10305 の反応式
[Cl:1][C:2]1[C:3]([NH:13][CH:14]2[CH2:16][CH2:15]2)=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[C:5]([OH:7])=O.[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[NH:18][NH2:19].C(N=C=NCCCN(C)C)C>ClCCl>[C:22]([O:21][C:17]([N:18]([C:5](=[O:7])[C:4]1[CH:8]=[C:9]([F:12])[C:10]([F:11])=[C:2]([Cl:1])[C:3]=1[NH:13][CH:14]1[CH2:16][CH2:15]1)[NH2:19])=[O:20])([CH3:25])([CH3:24])[CH3:23]

参加物

5

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 219789333-Chloro-2-cyclopropylamino-4,5-difluorobenzoic acid

生成物 1

HCID 86591203(3-Chloro-2-cyclopropylamino-4,5-difluorobenzoyl)-hydrazinecarboxylic acid tert-butyl ester収率 63.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3-chloro-2-cyclopropylamino-4,5-difluorobenzoic acid (Example 5d, 2.09 g, 8.45 mmol) in dichloromethane (30 mL) is added tert-butyl carbazate (1.67 g, 12.7 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (2.43 g, 12.7 mmol). After 16 hours, the reaction mixture is diluted with dichloromethane and washed with saturated NaHCO3, water, and brine. The organic layer is dried over MgSO4 and filtered. The filtrate is concentrated under vacuum and purified via flash column chromatography (1:2 ethyl acetate/hexanes) to afford the title compound (1.93 g). MS EI: m/z 360 (M+).

後処理

  1. washwashed with saturated NaHCO3, water, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under vacuum
  5. custompurified via flash column chromatography (1:2 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-2215a032e5f9454f83cc5b8245d8b56f
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

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