1,2-Dichloroethane → HCID 178513591, compound

HRID 1012073Notes

Reaction equation

HRID 1012073 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][C:19]([C:21]([OH:23])=O)=[CH:20][C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5].C(Cl)CCl.C1C=CC2N(O)N=[N:39]C=2C=1.C(N(C(C)C)CC)(C)C.[Cl-].[NH4+]>CN(C=O)C.O>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][C:19]([C:21]([NH2:39])=[O:23])=[CH:20][C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178524163HCID 178524163, compound

Product 1

HCID 178513591HCID 178513591, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-[4-(2,6-difluoro-benzoylamino)-1H-pyrazol-3-yl]-1H-benzimidazole-5-carboxylic acid (100 mg, 0.26 mmol), EDC (75 mg, 0.39 mmol) and HOBt (53 mg, 0.39 mmol) in DMF (1.5 ml) was successively added diisopropylethylamine (0.15 ml, 1.04 mmol) and ammonium chloride (28 mg, 0.52 mmol). The mixture was stirred at ambient temperature for 48 h and then reduced in vacuo. Water was added and the precipitate formed collected by filtration and dried through azeotrope with toluene to afford 2-[4-(2,6-difluoro-benzoylamino)-1H-pyrazol-3-yl]-1H-benzimidazole-5-carboxylic acid amide (49 mg, 49%) as a beige solid. (LC/MS: Rt 2.54, [M+H]+ 382.99).

Workup

  1. customthe precipitate formed
  2. filtrationcollected by filtration
  3. dry with materialdried through azeotrope with toluene

Sources & evidence

ORD record
ord-e5c622c47e384de2b529789c4f2bbafe
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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