1,2-Dichloroethane → (E)-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}pyrazine-2-carboxamide

HRID 1821322Notes

Reaction equation

HRID 1821322 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[N:2]1.[N:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[C:25](O)=[O:26].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl.C(=O)([O-])O.[Na+]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:25]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][N:19]=2)=[O:26])=[N:2]1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 10472-Pyrazinecarboxylic acidHCID 79724-MethylmorpholineHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 69001756HCID 69001756, compound

Product 1

HCID 69004090(E)-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}pyrazine-2-carboxamideYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-2-[2-(1H-indazol-3-yl)vinyl]phenylamine (60 mg, 0.26 mmol) was dissolved in THF (5 mL) and the solution was added with 2-pyrazinecarboxylic acid (38 mg, 0.31 mmol), 1-hydroxybenzotriazole monohydrate (51 mg, 0.33 mmol), 4-methylmorpholine (47 μL, 0.51 mmol) and EDC (68 mg, 0.36 mmol), followed by stirring at room temperature for 3 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in ethanol to obtain Compound 28 (25 mg, 30%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was triturated in ethanol

Sources & evidence

ORD record
ord-98a57dacc1a44ca6860685d2fe1b6661
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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