Trifluoroacetic acid → N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-methoxypyrimidin-4-yl]piperazine-1-sulfonamide, trifluoroacetate salt

HRID 2388777Notes

Reaction equation

HRID 2388777 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:34][CH3:35])[N:12]=1.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>ClCCl>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:34][CH3:35])[N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670512451,1-Dimethylethyl 4-[2-[[(2,3-difluorophenyl)methyl]thio)-6-methoxypyrimidin-4-yl sulfamoyl]piperazine-1-carboxylate

Product 1

HCID 67051309N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-methoxypyrimidin-4-yl]piperazine-1-sulfonamide, trifluoroacetate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4-[2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidin-4-yl sulfamoyl]piperazine-1-carboxylate (the product of step i) (0.36 g) and trifluoroacetic acid (1 mL) in dichloromethane (4 mL) were stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure and the residue was azeotroped with toluene (3×). The residual pale yellow solid was triturated with EtOAc, filtered and dried at 40° C. under high vacuum to give the title compound as a cream solid. Yield: 0.24 g.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was azeotroped with toluene (3×)
  3. customThe residual pale yellow solid was triturated with EtOAc
  4. filtrationfiltered
  5. customdried at 40° C. under high vacuum

Sources & evidence

ORD record
ord-71bc328ee7a74941bb9064d7c44fddfb
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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