4-Chlorobenzenesulfonyl chloride → HCID 10138168, compound

HRID 1643515Notes

Reaction equation

HRID 1643515 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]([OH:16])([C:12]([F:15])([F:14])[F:13])[C:8]([F:11])([F:10])[F:9])=[CH:5][N:6]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:1][C:2]2[S:3][C:4]([C:7]([OH:16])([C:8]([F:9])([F:10])[F:11])[C:12]([F:15])([F:13])[F:14])=[CH:5][N:6]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 23180662-(2-AMINO-1,3-THIAZOL-5-YL)-1,1,1,3,3,3-HEXAFLUOROPROPAN-2-OL

Product 1

HCID 10138168HCID 10138168, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2-amino-1,3-thiazol-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol (79.8 mg 0.3 mmol) from step 1 of example 1-1-1 in pyridine (1 ml) was added 4-chlorobenzensulfonyl chloride 63.3 mg (0.3 mmol). The reaction mixture was stirred at r.t. for 24 h. Pyridine was removed under reduced pressure to yield the residue, which was washed with 1N HCl to give a light brown solid. The solid was washed by water, saturated NaHCO3, brine, and dried by vacuum. Further purification by preparative TLC(CHCl3:CH3OH, 90:10) afforded the title compound as a white solid (38.2 mg). 1H NMR (DMSO-d6) δ7.55 (s, 1H), 7.60 (d, 2H), 7.78 (d, 2H), 9.50 (s, 1H), 13.2 (brs, 1H); ESIMS: m/z 439 (M−H).

Workup

  1. customPyridine was removed under reduced pressure
  2. customto yield the residue, which
  3. washwas washed with 1N HCl
  4. customto give a light brown solid
  5. washThe solid was washed by water, saturated NaHCO3, brine
  6. customdried by vacuum
  7. customFurther purification by preparative TLC(CHCl3:CH3OH, 90:10)

Sources & evidence

ORD record
ord-a40c310f1ed44974a7afc834d0a60975
Source dataset
uspto-grants-2012_02
Patent number
US08119819B2

Reaction notes

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