Pyridine → HCID 22716470, compound

HRID 1108593Notes

Reaction equation

HRID 1108593 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][F:17])[C:11](=[O:18])[CH2:10]2)=[C:6]([F:8])[CH:7]=1.N1C=CC=CC=1.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>ClCCl>[CH2:29]([O:28][C:26]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][F:17])[C:11](=[O:18])[CH2:10]2)=[C:6]([F:8])[CH:7]=1)=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 22716472HCID 22716472, compound

Product 1

HCID 22716470HCID 22716470, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

NMR (CDCl3) δ: 3.28 (t, 2H); 3.58 (t, 2H); 3.61 (br s, 2H); 3.68 (t, 1H); 3.72 (s, 2H); 3.80 (t, 1H); 4.56 (t, 1H); 4.75 (t, 1H); 6.40 (dd, 1H); 6.44 (dd, 1H); 6.78 (t, 1H). 5-Amino-2-(4-{2-fluoroethyl}-3-oxopiperazin-1-yl)fluorobenzene (2.6 g) was dissolved in dry dichloromethane (50 ml) under argon. Pyridine (1.03 ml) was added, and the mixture cooled to -20° C. Benzyl chloroformate (1.6 ml) was added, and the mixture stirred for 10 minutes at -20° C., before allowing the temperature to rise to ambient over 1.5 hours. Solvents were evaporated, the residue dissolved in dichloromethane and washed with sodium bicarbonate solution. After drying (MgSO4) and evaporation of solvent, the residue was chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give 5-benzyloxycarbonylamino-2-(4-{2-fluoroethyl}-3-oxopiperazin-1-yl)fluorobenzene (3.43 g).

Workup

  1. waitto ambient over 1.5 hours
  2. customSolvents were evaporated
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with sodium bicarbonate solution
  5. customAfter drying
  6. custom(MgSO4) and evaporation of solvent
  7. customthe residue was chromatographed on silica
  8. temperaturea gradient increasing in polarity from 0 to 5% methanol in dichloromethane
  9. customevaporated

Sources & evidence

ORD record
ord-d91efed6a4ff4b2fbadd9b5f12243c29
Source dataset
uspto-grants-2000_05
Patent number
US06069145

Reaction notes

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