4-Toluenesulfonyl chloride → HCID 86610854, compound

HRID 2105236Notes

Reaction equation

HRID 2105236 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][C:14]1[N:19]=[C:18]([N:20]2[CH2:24][CH2:23][CH2:22][CH:21]2[C:25]2[O:29][N:28]=[C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[CH:26]=2)[N:17]=[C:16]([NH:36][C:37]2[CH:41]=[C:40]([CH3:42])[NH:39][N:38]=2)[CH:15]=1.C(N([CH2:48][CH3:49])CC)C>C1COCC1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][C:14]2[N:19]=[C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH:21]3[C:25]3[O:29][N:28]=[C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)[CH:26]=3)[N:17]=[C:16]([NH:36][CH:37]3[CH:41]=[C:40]([CH3:42])[NH:39][N:38]3[S:7]([C:4]3[CH:5]=[CH:6][C:48]([CH3:49])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[CH:15]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11350611HCID 11350611, compound

Product 1

HCID 86610854HCID 86610854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Toluenesulphonyl chloride (3.0 g, 15.7 mmol) was added to a mixture of 6-hydroxymethyl-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Example 80) (3.13 g, 7.49 mmol), triethylamine (2.5 ml, 18 mmol) in anhydrous THF (50 ml). The resulting mixture was stirred at ambient temperature for 1 hour then heated at reflux for 4 hours. The volatiles were removed by evaporation and the residue dissolved in water and extracted with DCM. The organic extracts were combined and the solvent removed by evaporation. The residue was purification by chromatography on silica gel, eluting with DCM (100%) and then with diethylether (100%) to give the title compound (contaminated with 31% of the 6-chloromethyl derivative) (1.69 g, 31%).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 4 hours
  3. customThe volatiles were removed by evaporation
  4. dissolutionthe residue dissolved in water
  5. extractionextracted with DCM
  6. customthe solvent removed by evaporation
  7. custompurification by chromatography on silica gel
  8. washeluting with DCM (100%)

Sources & evidence

ORD record
ord-090ce5a9e1264f8388720777eaa050d1
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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