1,2-Dichloroethane → HCID 178522426, compound

HRID 1012094Notes

Reaction equation

HRID 1012094 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12](O)=O)=[N:9][NH:10][CH:11]=1)=[O:5].[N:20]1([CH2:26][C:27]2[CH:28]=[C:29]([NH2:34])[C:30]([NH2:33])=[CH:31][CH:32]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]2[NH:33][C:30]3[CH:31]=[CH:32][C:27]([CH2:26][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:28][C:29]=3[N:34]=2)=[N:9][NH:10][CH:11]=1)=[O:5]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 251933094-(Morpholinomethyl)benzene-1,2-diamineHCID 178524952HCID 178524952, compound

Product 1

HCID 178522426HCID 178522426, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid (75 mg, 0.25 mmol), 4-morpholin-4-ylmethyl-benzene-1,2-diamine (52 mg, 0.25 mmol), EDC (58 mg, 0.3 mmol) and HOBt (41 mg, 0.3 mmol) in DMF (4 ml) was stirred at ambient temperature for 48 hours. The mixture was partitioned between EtOAc and saturated aqueous NaHCO3 and the organic portion washed with saturated aqueous NH4Cl, dried (MgSO4) and reduced in vacuo. The residue was taken up in AcOH and heated at 100° C. for 14 hours. cooled to ambient temperature and reduced in vacuo. The residue was purified via flash column chromatography eluting with CH2Cl2-MeOH (20:1-10:1) to give 2,6-dichloro-N-[3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (30 mg) as a pink solid. (LC/MS: Rt 2.12, [M+H]+ 471.14).

Workup

  1. customThe mixture was partitioned between EtOAc and saturated aqueous NaHCO3
  2. washthe organic portion washed with saturated aqueous NH4Cl
  3. dry with materialdried (MgSO4)
  4. temperatureheated at 100° C. for 14 hours
  5. temperaturecooled to ambient temperature
  6. customThe residue was purified via flash column chromatography
  7. washeluting with CH2Cl2-MeOH (20:1-10:1)

Sources & evidence

ORD record
ord-4e1e6bfbe74e4ce9a9f3bac4b83db5b9
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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