1,2-Dichloroethane → N2-(4-t-Butylbenzoyl)-N1-(6-indazolylcarbonyl)-1,2-benzenediamine

HRID 842367Notes

Reaction equation

HRID 842367 reaction equation
[C:1]([C:5]1[CH:20]=[CH:19][C:8]([C:9]([NH:11][C:12]2[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:30](O)=[O:31])[CH:28]=2)[CH:23]=[N:22]1.C(Cl)CCl>CN(C=O)C>[C:1]([C:5]1[CH:20]=[CH:19][C:8]([C:9]([NH:11][C:12]2[C:13]([NH:18][C:30]([C:27]3[CH:28]=[C:29]4[C:24]([CH:23]=[N:22][NH:21]4)=[CH:25][CH:26]=3)=[O:31])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 1133079N-(2-aminophenyl)-4-tert-butylbenzamideHCID 162279381H-indazole-6-carboxylic acid

Product 1

HCID 12015825N2-(4-t-Butylbenzoyl)-N1-(6-indazolylcarbonyl)-1,2-benzenediamineYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of N2-(4-t-butylbenzoyl)-1,2-benzenediamine (830 mg, 3.1 mmol) and 6-indazolecarboxylic acid (European Pat. Appln. Pub. No. 242 167 A2, p 43) (500 mg, 3.1 mmol) in DMF (5 mL) was added EDC (1.19 g, 6.2 mmol). After 12 h, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate and washed twice with water and twice with brine. The organic phase was dried with MgSO4, filtered and concentrated in vacuo, then chromatographed over silica gel, eluting with a solvent gradient of dichloromethane through 5% methanol/dichloromethane. The product containing fractions were combined and concentrated in vacuo to give 330 mg (26%) of an off-white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed twice with water and twice with brine
  4. dry with materialThe organic phase was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customchromatographed over silica gel
  8. washeluting with a solvent gradient of dichloromethane through 5% methanol/dichloromethane
  9. additionThe product containing fractions
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99e6c7e3340548ae922c05c7e17eb984
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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