1,2-Dichloroethane → HCID 178499178, compound

HRID 1012158Notes

Reaction equation

HRID 1012158 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:15][O:16][C:17]([C:19]1[C:23]([NH2:24])=[CH:22][NH:21][N:20]=1)=[O:18].[C:25]([C:29]1[CH:30]=[CH:31][C:32]([O:38][CH3:39])=[C:33]([CH:37]=1)[C:34](O)=[O:35])([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[CH3:15][O:16][C:17]([C:19]1[C:23]([NH:24][C:34](=[O:35])[C:33]2[CH:37]=[C:29]([C:25]([CH3:26])([CH3:27])[CH3:28])[CH:30]=[CH:31][C:32]=2[O:38][CH3:39])=[CH:22][NH:21][N:20]=1)=[O:18]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 70103155-Tert-Butyl-2-Methoxybenzoic AcidHCID 178499176HCID 178499176, compound

Product 1

HCID 178499178HCID 178499178, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EDC (11.59 g, 60.7 mmol), HOBt (8.19 g, 60.7 mmol) and 4-amino-1H-pyrazole-3-carboxylic acid methyl ester (7.84 g, 55.6 mmol) in DMF (100 ml) was added 5-tert-butyl-2-methoxy-benzoic acid (10.52 g, 50.6 mmol) and the mixture stirred at room temperature overnight. The mixture was reduced in vacuo and the residue partitioned between EtOAc (500 ml) and brine (200 ml), the organic portion was washed with saturated aqueous sodium hydrogen carbonate (200 ml), dried (MgSO4) and reduced in vacuo to yield 4-(5-tert-butyl-2-methoxy-benzoylamino)-1H-pyrazole-3-carboxylic acid methyl ester as a pale yellow solid (17.07 g, 93%). (LC/MS (acidic method): Rt 3.12 min, [M+H]+ 332).

Workup

  1. customthe residue partitioned between EtOAc (500 ml) and brine (200 ml)
  2. washthe organic portion was washed with saturated aqueous sodium hydrogen carbonate (200 ml)
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-57a837cddb3942a1a32a23ad8212dee0
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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