1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N2-(2-cyclopropylamino-4,5-difluorobenzoyl)hydrazinecarboxylic acid tert-butyl ester

HRID 10303

Reaction equation

HRID 10303 reaction equation
[CH:1]1([NH:4][C:5]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:6]=2[C:7]([OH:9])=O)[CH2:3][CH2:2]1.[C:16]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[NH:17][NH2:18].C(N=C=NCCCN(C)C)C>ClCCl>[C:21]([O:20][C:16]([NH:17][NH:18][C:7](=[O:9])[C:6]1[CH:10]=[C:11]([F:15])[C:12]([F:14])=[CH:13][C:5]=1[NH:4][CH:1]1[CH2:2][CH2:3]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 149974732-Cyclopropylamino-4,5-difluorobenzoic acid

Product 1

HCID 21860880N2-(2-cyclopropylamino-4,5-difluorobenzoyl)hydrazinecarboxylic acid tert-butyl esterYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-cyclopropylamino-4,5-difluorobenzoic acid (Example 5) (1.32 g, 6.19 mmol) and tert-butyl carbazate (1.30 g, 9.75 mmol) in dichloromethane (30 mL) is added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (1.87 g, 9.75 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 N2-(2-cyclopropylamino-4,5-difluorobenzoyl)hydrazinecarboxylic acid tert-butyl ester as a solid (1.65 g). MS EI: m/z 328 (M+).

Workup

  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)

Sources & evidence

ORD record
ord-d6dea635e510434eb027e992714d250b
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Linked notes

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