1,2-Dichloroethane → HCID 178490078, compound

HRID 1012159Notes

Reaction equation

HRID 1012159 reaction equation
C(Cl)CCl.[CH:5]1[CH:6]=[CH:7][C:8]2[N:13](O)N=[N:11][C:9]=2[CH:10]=1.[C:15]([C:19]1[CH:20]=[CH:21][C:22]([O:36][CH3:37])=[C:23]([CH:35]=1)[C:24]([NH:26][C:27]1[C:28]([C:32](O)=[O:33])=[N:29][NH:30][CH:31]=1)=[O:25])([CH3:18])([CH3:17])[CH3:16].C1(N)C(N)=CC=CC=1>CN(C=O)C>[NH2:13][C:8]1[CH:7]=[CH:6][CH:5]=[CH:10][C:9]=1[NH:11][C:32]([C:28]1[C:27]([NH:26][C:24](=[O:25])[C:23]2[CH:35]=[C:19]([C:15]([CH3:16])([CH3:17])[CH3:18])[CH:20]=[CH:21][C:22]=2[O:36][CH3:37])=[CH:31][NH:30][N:29]=1)=[O:33]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 178490079HCID 178490079, compound

Product 1

HCID 178490078HCID 178490078, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EDC (720 mg, 3.8 mmol), HOBt (510 mg, 3.8 mmol) and 4-(5-tert-butyl-2-methoxy-benzoylamino)-1H-pyrazole-3-carboxylic acid (1 g, 3.16 mmol) in DMF (25 ml) was added benzene-1,2-diamine (375 mg, 3.5 mmol) and the mixture stirred at room temperature for 5 hours. The mixture was reduced in vacuo and the residue partitioned between EtOAc (50 ml) and brine (2×50 ml). Undissolved precipitate was removed by filtration, the organic portions washed with saturated aqueous sodium hydrogen carbonate (50 ml), dried (MgSO4) and reduced in vacuo to yield 4-(5-tert-butyl-2-methoxy-benzoylamino)-1H-pyrazole-3-carboxylic acid (2-amino-phenyl)-amide as a pale yellow powder (848 mg, 66%). (LC/MS (acidic method): Rt 3.21 min, [M+H]+ 408).

Workup

  1. customthe residue partitioned between EtOAc (50 ml) and brine (2×50 ml)
  2. customUndissolved precipitate was removed by filtration
  3. washthe organic portions washed with saturated aqueous sodium hydrogen carbonate (50 ml)
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-0be4dff3c5eb4accb630cb16d18ae58c
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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