Diethyl Ether → methyl [(2,5-difluorophenyl)sulfonyl]{3-[1-ethyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]-2,4-difluorophenyl}carbamate

HRID 1631545Notes

Reaction equation

HRID 1631545 reaction equation
[F:1][C:2]1[C:7]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][N:10]([CH2:19][CH3:20])[N:9]=2)=[C:6]([F:21])[CH:5]=[CH:4][C:3]=1[NH:22][S:23]([C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[F:33])(=[O:25])=[O:24].Cl[C:35]([O:37][CH3:38])=[O:36].C(OCC)C>C(Cl)Cl.O>[F:33][C:27]1[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=1[S:23]([N:22]([C:3]1[CH:4]=[CH:5][C:6]([F:21])=[C:7]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)=[CH:11][N:10]([CH2:19][CH3:20])[N:9]=2)[C:2]=1[F:1])[C:35](=[O:36])[O:37][CH3:38])(=[O:24])=[O:25]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6586Methyl chloroformateHCID 44622209N-{2,4-difluoro-3-[1-ethyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-2,5-difluorobenzenesulfonamide

Product 1

HCID 53328042methyl [(2,5-difluorophenyl)sulfonyl]{3-[1-ethyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]-2,4-difluorophenyl}carbamateYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-{2,4-difluoro-3-[1-ethyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-2,5-difluorobenzenesulfonamide (80 mg, 0.168 mmol) was suspended in 3.5 mL of DCM and TEA (18.7 mg, 25.8 μL, 0.185 mmol) was added. Methyl chloroformate (17.5 mg, 13.0 L, 0.185 mmol) was added to the solution so obtained, and the reaction mixture was stirred at room temperature for 3 hours, diluted with DCM, and poured in water. The organic layer was washed three times with water, once with brine, dried over Na2SO4 and concentrated to dryness. The solid so obtained was taken up with ethyl ether and filtered (72 mg, 80% yield)

Workup

  1. customso obtained
  2. washThe organic layer was washed three times with water
  3. dry with materialonce with brine, dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe solid so obtained
  6. filtrationfiltered (72 mg, 80% yield)

Sources & evidence

ORD record
ord-87b068699d4b45e1bf5ac0dd96d70e98
Source dataset
uspto-grants-2014_07
Patent number
US08791265B2

Reaction notes

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