1,2-Dichloroethane → HCID 51357792, compound

HRID 1623792Notes

Reaction equation

HRID 1623792 reaction equation
[NH:1]1[CH:5]=[C:4]([NH2:6])[CH:3]=[N:2]1.[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:12]([CH:16]=1)[C:13](O)=[O:14].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:12]([CH:16]=1)[C:13]([NH:6][C:4]1[CH:5]=[N:1][NH:2][CH:3]=1)=[O:14]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 780351H-pyrazol-4-amineHCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Product 1

HCID 51357792HCID 51357792, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Neat 1H-pyrazol-4-amine (55.2 mg, 0.66 mmol) was added in one charge to a stirred solution of 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method D; 170 mg, 0.55 mmol), EDC (318 mg, 1.66 mmol) and HOBT (254 mg, 1.66 mmol) in N,N-dimethylformamide (4 ml) in air at room temperature. The reaction mixture was stirred at room temperature overnight. Water (30 ml) was added, and the mixture was extracted with ethyl acetate (50 ml×2). The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The residue was washed with ethyl acetate yield the title compound as a brown solid. 180 mg.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 ml×2)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-ddd0d1db279c465e86aa19e991c6fc6c
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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