Pyridine → HCID 22716470, compound

HRID 1365580Notes

Reaction equation

HRID 1365580 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

Procedure

5-Amino-2-(4-[2-fluoroethyl]-3-oxopiperazin-1-yl)fluorobenzene (2.6 g) is dissolved in dry dichloromethane (50 ml) under argon. Pyridine (1.03 ml) is added, and the mixture cooled to −20°. Benzyl chloroformate (1.6 ml) is added and the mixture stirred for 10 minutes at −20°, before allowing the temperature to rise to 20–25° over 1.5 hours. The solvents are removed and the residue is dissolved in dichloromethane and washed with sodium bicarbonate solution. After drying over magnesium sulfate and removal of the solvent, the residue is chromatographed (silica, eluting with a gradient increasing in polarity from 0 to 5% methanol in dichloromethane) to give 5-benzyloxycarbonylamino-2-(4-[2-fluoroethyl]-3-oxopiperazin-1-yl)fluorobenzene.

Workup

  1. temperaturethe mixture cooled to −20°
  2. waitto rise to 20–25° over 1.5 hours
  3. customThe solvents are removed
  4. dissolutionthe residue is dissolved in dichloromethane
  5. washwashed with sodium bicarbonate solution
  6. dry with materialAfter drying over magnesium sulfate and removal of the solvent
  7. customthe residue is chromatographed (silica
  8. washeluting with a gradient
  9. temperatureincreasing in polarity from 0 to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a2cc73f6e90f4e66853c6933260ae822
Source dataset
uspto-grants-2011_02
Patent number
US07892574B2

Reaction notes

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