1,2-Dichloroethane → HCID 178486787, compound

HRID 1012146Notes

Reaction equation

HRID 1012146 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:15][O:16][C:17]1[C:31]([O:32][CH3:33])=[CH:30][C:20]2[NH:21][C:22]([C:24]3[C:28]([NH2:29])=[CH:27][NH:26][N:25]=3)=[N:23][C:19]=2[CH:18]=1.[F:34][C:35]1[CH:36]=[CH:37][C:38]([O:44][CH3:45])=[C:39]([CH:43]=1)[C:40](O)=[O:41]>CN(C=O)C>[CH3:33][O:32][C:31]1[C:17]([O:16][CH3:15])=[CH:18][C:19]2[NH:23][C:22]([C:24]3[C:28]([NH:29][C:40](=[O:41])[C:39]4[CH:43]=[C:35]([F:34])[CH:36]=[CH:37][C:38]=4[O:44][CH3:45])=[CH:27][NH:26][N:25]=3)=[N:21][C:20]=2[CH:30]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27373645-Fluoro-2-methoxybenzoic acidHCID 178486794HCID 178486794, compound

Product 1

HCID 178486787HCID 178486787, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EDC (44 mg, 0.23 mmol) and HOBt (31 mg, 0.23 mmol) in DMF (5 ml) was added 3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (50 mg, 0.19 mmol) and 5-fluoro-2-methoxy-benzoic acid (36 mg, 0.21 mmol) and the mixture stirred at room temperature overnight. The solvent was removed in vacuo and the resulting solid partitioned between DCM (20 ml) and saturated aqueous sodium bicarbonate (20 ml). A precipitate was formed which was removed by filtration and oven dried to yield N-[3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-5-fluoro-2-methoxy-benzamide (64 mg, 81%). (LC/MS: Rt 2.64, [M+H]+ 412).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting solid partitioned between DCM (20 ml) and saturated aqueous sodium bicarbonate (20 ml)
  3. customA precipitate was formed which
  4. customwas removed by filtration and oven
  5. customdried

Sources & evidence

ORD record
ord-777f532edc1045558b7ca0fecfe80926
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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