4-Toluenesulfonyl chloride → HCID 58804025, compound

HRID 349278Notes

Reaction equation

HRID 349278 reaction equation
C1(C)C=CC(S([Cl:10])(=O)=O)=CC=1.C(N(CC)CC)C.[F:19][C:20]([F:60])([F:59])[C:21]1[CH:22]=[C:23]([CH:52]=[C:53]([C:55]([F:58])([F:57])[F:56])[CH:54]=1)[CH2:24][N:25]1[C:29]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[C:28]([C:36]([C:38]2[C:39]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[Cl:51])=[N:40][O:41][C:42]=2[CH2:43]O)=[O:37])[N:27]=[N:26]1>ClCCl.C1COCC1>[F:56][C:55]([F:58])([F:57])[C:53]1[CH:52]=[C:23]([CH:22]=[C:21]([C:20]([F:59])([F:60])[F:19])[CH:54]=1)[CH2:24][N:25]1[C:29]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[C:28]([C:36]([C:38]2[C:39]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[Cl:51])=[N:40][O:41][C:42]=2[CH2:43][Cl:10])=[O:37])[N:27]=[N:26]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86601234HCID 86601234, compound

Product 1

HCID 58804025HCID 58804025, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add N,N-dimethylaminopyridine (119 mg, 0.974 mmol), p-toluenesulfonyl chloride (465 mg, 2.44 mmol) and triethylamine into an ice-cold solution of [1-(3,5-bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1H-[1,2,3]triazol-4-yl]-[3-(2-chlorophenyl)-5-hydroxymethyl-isoxazol-4-yl]-methanone (1.0 g, 1.62 mmol) in dichloromethane (5.0 mL) and THF (5.0 mL). Warm the mixture to RT. After 1 h., concentrate in vacuo. Dilute the mixture with dichloromethane (50 mL) and wash with water (3×40 mL). Dry (MgSO4), filter, and concentrate in vacuo. Purify the residue by flash chromatography on silica gel to provide the title compound (59% yield) as a brown oil. MS (ES) 634.1 (M++1); TLC Rf=0.5 (50% EtOAc in hexanes).

Workup

  1. concentrationconcentrate in vacuo
  2. additionDilute the mixture with dichloromethane (50 mL)
  3. washwash with water (3×40 mL)
  4. dry with materialDry (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3174f0f321144869b44d96fd1ec2869e
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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