1,2-Dichloroethane → HCID 178522429, compound

HRID 1012141Notes

Reaction equation

HRID 1012141 reaction equation
[N:1]1[O:2][C:3]([C:10]([OH:12])=O)=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[N:13]1([CH2:19][C:20]2[CH:34]=[CH:33][C:23]3[NH:24][C:25]([C:27]4[C:31]([NH2:32])=[CH:30][NH:29][N:28]=4)=[N:26][C:22]=3[CH:21]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[N:13]1([CH2:19][C:20]2[CH:34]=[CH:33][C:23]3[NH:24][C:25]([C:27]4[C:31]([NH:32][C:10]([C:3]5[O:2][N:1]=[C:5]6[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=56)=[O:12])=[CH:30][NH:29][N:28]=4)=[N:26][C:22]=3[CH:21]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 258162Anthroxanic acidHCID 178508054HCID 178508054, compound

Product 1

HCID 178522429HCID 178522429, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of benzo[c]isoxazole-3-carboxylic acid (46 mg, 0.28 mmol), 3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (100 mg, 0.33 mmol), EDC (64 mg, 0.33 mmol) and HOBt (45 mg, 0.33 mmol) was stirred at room temperature in DMF (2.5 ml) for 20 h. The mixture was reduced in vacuo and the residue partitioned between EtOAc (5 ml) and water (2 ml), the organic portion washed with saturated aqueous sodium hydrogen carbonate, dried (MgSO4) and reduced in vacuo. The residue was purified by flash column chromatography [SiO2, EtOAc-MeOH (100:0-90:10)] to give benzo[c]isoxazole-3-carboxylic acid[3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-amide as a white solid (40 mg, 32%). (LC/MS: Rt 2.13, [M+H]+ 444).

Workup

  1. customthe residue partitioned between EtOAc (5 ml) and water (2 ml)
  2. washthe organic portion washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried (MgSO4)
  4. customThe residue was purified by flash column chromatography [SiO2, EtOAc-MeOH (100:0-90:10)]

Sources & evidence

ORD record
ord-05b584c7119e4f4aa59185fae0018a49
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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