1,2-Dichloroethane → HCID 18373180, compound

HRID 2301826Notes

Reaction equation

HRID 2301826 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[C:14]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH2:30])[CH:28]=2)[CH:23]=[N:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(Cl)CCl>CN(C=O)C>[C:14]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH:30][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[C:3]=3[N+:11]([O-:13])=[O:12])[CH:28]=2)[CH:23]=[N:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 215753-Methyl-2-nitrobenzoic acidHCID 120186071-BOC-6-AMINO-INDAZOLE

Product 1

HCID 18373180HCID 18373180, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 3-methyl-2-nitrobenzoic acid (1.8 g, 10.1 mmol) and 1-Boc-6-amino-indazole (2.37 g, 10.1 mmol) in DMF (20 mL) was added EDC (3.17 g, 15.2 mmol). After stirring for 16 h, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and 1 M citric acid. The layers were separated and the organic phase was washed again with 1 M citric acid, once with water, twice with satd aq NaHCO3, and once with brine. The organic phase was then dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in a minimal volume of chloroform and chromatographed over silica gel, eluting with a gradient of 40% ethyl acetate/hexanes through 70% ethyl acetate/hexanes. The product containing fractions were combined and concentrated in vacuo to give 2.34 g (58%) of off-white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and 1 M citric acid
  3. customThe layers were separated
  4. washthe organic phase was washed again with 1 M citric acid, once with water, twice with satd aq NaHCO3
  5. dry with materialThe organic phase was then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in a minimal volume of chloroform
  9. customchromatographed over silica gel
  10. washeluting with a gradient of 40% ethyl acetate/hexanes through 70% ethyl acetate/hexanes
  11. additionThe product containing fractions
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c9cb1964510422593ba9e86cd879379
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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