1,2-Dichloroethane → HCID 67107332, compound

HRID 1623805Notes

Reaction equation

HRID 1623805 reaction equation
[NH:1]1[CH:5]=[C:4]([NH2:6])[CH:3]=[N:2]1.[C:7]1([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[CH:20][C:16]=2[C:17](O)=[O:18])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.CC#N.O>[C:7]1([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)=[CH:20][C:16]=2[C:17]([NH:6][C:4]2[CH:5]=[N:1][NH:2][CH:3]=2)=[O:18])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 780351H-pyrazol-4-amineHCID 669904822-(Benzyloxy)-5-(pyridin-4-yl)benzoic acid

Product 1

HCID 67107332HCID 67107332, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Neat 1H-pyrazol-4-amine (49.0 mg, 0.59 mmol) was added in one charge to a stirred solution of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 150 mg, 0.49 mmol), EDC (283 mg, 1.47 mmol) and HOBT (226 mg, 1.47 mmol) in dimethylformamide (4 ml) in air at room temperature. The reaction mixture was stirred at room temperature overnight. 30 ml water was added, and the mixture was extracted with ethyl acetate (70 ml×2). The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The residue was further purified by pre-HPLC (Gilson GX-281; Shimadzu 15 μm 250*20 mm; A: 10 mMol NH4HCO3/Water; B: CH3CN) to yield the title compound as a white solid. 50 mg.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (70 ml×2)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was further purified by pre-HPLC (Gilson

Sources & evidence

ORD record
ord-f8e20d1440a54050aaf06939cde31582
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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