Pyridine → HCID 10810357, compound

HRID 654795Notes

Reaction equation

HRID 654795 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)=[CH:16][C:15]([NH2:28])=[N:14]2)=[CH:9][CH:8]=1.N1C=CC=CC=1>C(#N)C.O1CCCC1.C(OCC)(=O)C>[F:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)=[CH:16][C:15]([NH:28][C:2](=[O:3])[O:4][CH3:5])=[N:14]2)=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 10782725HCID 10782725, compound

Product 1

HCID 10810357HCID 10810357, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

Methyl chloroformate (0.163 ml) in acetonitrile (0.7 ml) was added dropwise to a stirred solution of 1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-amine (0.7 g) and pyridine (0.171 ml) in acetonitrile (6 ml) and tetrahydrofuran (7 ml) at -20° C. The mixture was stirred at 5° C. for 1 hour, diluted with ethyl acetate, washed with water, dried, and concentrated. The residue (0.9 g) was recrystallized from a mixture of chloroform and ethanol to give pale brown crystals of methyl N-{1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-3-pyrazolyl}carbamate (0.51 g).

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue (0.9 g) was recrystallized from a mixture of chloroform and ethanol

Sources & evidence

ORD record
ord-05f74a75a5e04893835e005ee5798b07
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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