1,2-Dichloroethane → HCID 69936460, compound

HRID 1623806Notes

Reaction equation

HRID 1623806 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH2:7])[CH:4]=[N:3]1.[C:8]1([CH2:14][O:15][C:16]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[CH:21][C:17]=2[C:18](O)=[O:19])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:18](=[O:19])[C:17]2[CH:21]=[C:22]([C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)[CH:23]=[CH:24][C:16]=2[O:15][CH2:14][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 47709901-methyl-1H-pyrazol-4-amineHCID 669904822-(Benzyloxy)-5-(pyridin-4-yl)benzoic acid

Product 1

HCID 69936460HCID 69936460, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Neat 1-methyl-1H-pyrazol-4-amine (38.2 mg, 0.39 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; 100 mg, 0.33 mmol), EDC (188 mg, 0.98 mmol) and HOBT (150 mg, 0.983 mmol) in dimethylformamide (3 ml) in air at room temperature. The reaction mixture was stirred at room temperature overnight. Water (20 ml) was added, and the mixture was extracted with ethyl acetate (20 ml×2). The organic phase was dried over Na2SO4, and concentrated in vacuo to give crude product, which was purified by prep-HPLC (Gilson GX-281; waters X-Bridge 5 μm 30*100 mm; A: 0.1M NH3.H2O/Water; B: CH3CN) twice to yield the title compound as a white solid. 58 mg.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (20 ml×2)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give crude product, which
  5. customwas purified by prep-HPLC (Gilson

Sources & evidence

ORD record
ord-3cdf3a8335484108aea2e57b7ca8d928
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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