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

HRID 10304

Reaction equation

HRID 10304 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:6]=1[C:7]([OH:9])=O.[C:21]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:24])[NH:22][NH2:23].C(N=C=NCCCN(C)C)C>ClCCl>[C:26]([O:25][C:21]([N:22]([C:7](=[O:9])[C:6]1[CH:10]=[C:11]([F:15])[C:12]([F:14])=[CH:13][C:5]=1[NH:4][C:3]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:2]=1[F:1])[NH2:23])=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 149974752-(2,4-Difluoroanilino)-4,5-difluorobenzoic acid

Product 1

HCID 69071940[2-(2,4-Difluoroanilino)-4,5-difluorobenzoyl]-hydrazinecarboxylic acid tert-butyl esterYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2,4-difluoroanilino)-4,5-difluorobenzoic acid (Example 5, 2.18 g, 7.6 mmol) and tert-butyl carbazate (1.57 g, 11.8 mmol) in dichloromethane (30 mL) is added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (2.25 g, 11.77 mmol). After stirring for 16 hours at room temperature, the reaction mixture is diluted with dichloromethane and then washed with saturated NaHCO3, water, and brine. The organic layer is dried over Na2SO4, concentrated under vacuum, and purified via column chromatography (1:3 ethyl acetate/hexanes) to afford [2-(2,4-difluoroanilino)-4,5-difluorobenzoyl]-hydrazinecarboxylic acid tert-butyl ester as a solid (2.20 g). MS EI: m/z 400 (M+).

Workup

  1. washwashed with saturated NaHCO3, water, and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. custompurified via column chromatography (1:3 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-eeeb0d9ca8654a97b94c5952a45d29e4
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Linked notes

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