1,2-Dichloroethane → HCID 32609480, compound

HRID 1623791Notes

Reaction equation

HRID 1623791 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH2:7])[CH:4]=[N:3]1.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:13]([CH:17]=1)[C:14](O)=[O:15].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:13]([CH:17]=1)[C:14]([NH:7][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:15]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 24613572-(Benzyloxy)-5-bromobenzoic acidHCID 47709901-methyl-1H-pyrazol-4-amine

Product 1

HCID 32609480HCID 32609480, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Neat 1-methyl-1H-pyrazol-4-amine (61.7 mg, 0.64 mmol) was added in one charge to a stirred suspension of 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5; 150 mg, 0.49 mmol), EDC (281 mg, 1.47 mmol) and HOBT (224 mg, 1.47 mmol) in N,N-dimethylformamide (3 ml) in air at room temperature. The reaction mixture was stirred at room temperature overnight. 20 ml of water was added and the mixture was extracted with ethyl acetate (20 ml×2). The combined organic phases were 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: 0.1NH3*H2O/Water; B: CH3CN) twice to yield the title compound as a white solid. 70 mg.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (20 ml×2)
  2. dry with materialThe combined organic phases were 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-43af861d798540288d2c3fa373ec644b
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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