Dichloromethane → HCID 118046062, compound

HRID 596117Notes

Reaction equation

HRID 596117 reaction equation
[NH2:1][C:2]1[C:3]([C:14]2[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[C:16]([F:27])[CH:15]=2)=[N:4][C:5]([C:8]2[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=2)=[CH:6][N:7]=1.C(Cl)Cl>CO>[NH2:1][C:2]1[C:3]([C:14]2[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])=[C:16]([F:27])[CH:15]=2)=[N:4][C:5]([CH:8]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 118045740HCID 118045740, compound

Product 1

HCID 118046062HCID 118046062, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To tert-butyl 4-(3-amino-6-(3-oxocyclopent-1-en-1-yl)pyrazin-2-yl)-2-fluorobenzoate (650 mg, 1.760 mmol) in MeOH (15 ml) was added 15 ml of DCM under stirring until a clear solution was obtained. The solution was purged by nitrogen for 5 min, then Pd/C (300 mg, 10%, Degussa type) was added, and the resultant mixture was degassed by N2 stream for 15 min. After equipped with hydrogen gas balloon, the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was filtered, and the filtrated solution was concentrated, and the crude material was purified by ISCO. (24 g silica gel, 20 to 80% EtOAc in heptane) to afford 380 mg of the desired product as a light yellow solid. 58.1% yield. LC-MS (m/z): (MH+) 372.1, 0.829 min.

Workup

  1. customwas obtained
  2. customThe solution was purged by nitrogen for 5 min
  3. additionPd/C (300 mg, 10%, Degussa type) was added
  4. customthe resultant mixture was degassed by N2 stream for 15 min
  5. customAfter equipped with hydrogen gas balloon
  6. stirringthe reaction mixture was stirred at room temperature for 16 h
  7. filtrationThe reaction mixture was filtered
  8. concentrationthe filtrated solution was concentrated
  9. customthe crude material was purified by ISCO

Sources & evidence

ORD record
ord-62a276afb1554b8fa262cf2c7e620b3d
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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