4-Toluenesulfonyl chloride → HCID 86598687, compound

HRID 2375294Notes

Reaction equation

HRID 2375294 reaction equation
[OH:1][CH2:2][C:3]([NH:6][S:7]([C:10]1[CH:29]=[CH:28][C:13]([NH:14][C:15]2[N:20]=[C:19]([C:21]3[N:25]([CH3:26])[C:24]([CH3:27])=[N:23][CH:22]=3)[CH:18]=[CH:17][N:16]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])([CH3:5])[CH3:4].[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>N1C=CC=CC=1.O>[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36]([O:1][CH2:2][C:3]([NH:6][S:7]([C:10]2[CH:29]=[CH:28][C:13]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[N:25]([CH3:26])[C:24]([CH3:27])=[N:23][CH:22]=4)[CH:18]=[CH:17][N:16]=3)=[CH:12][CH:11]=2)(=[O:8])=[O:9])([CH3:5])[CH3:4])(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 69307815HCID 69307815, compound

Product 1

HCID 86598687HCID 86598687, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2-{4-[N-(1-Hydroxy-2-methylprop-2-yl)sulphamoyl]anilino}-4-(1,2-dimethylimidazol-5-yl)pyrimidine (Example 59; 2.36 g, 5.66 mmol) was dissolved in dry pyridine (55 ml) and the solution stirred and cooled to 0° C. under inert gas. Solid p-toluenesulphonyl chloride (5.61 g, 29.4 mmol) was added portionwise over 2 minutes. The reaction was stirred at 0° C. for 10 minutes and then at room temperature for 18 hr. The reaction mixture was diluted with water (200 ml) and the precipitated oil allowed to settle out. The supernatant water layer was decanted off and the residual oil was washed with more water and this was decanted off. This process was repeated and then the oil partitioned between EtOAc (100 ml) and water (50 ml). The layers were separated and the organic layer washed with water (50 ml), dried and the solvent evaporated in vacuo to yield the title compound as a gum (1.94 g, 60%) NMR 1.0 (s, 6H), 2.36 (s, 3H), 2.38 (s, 3H), 3.77 (s, 2H), 3.93 (s, 3H), 7.20 (d, 1H), 7.43 (d, 2H), 7.55 (s, 1H), 7.65 (m, 5H), 7.87 (d, 2H), 8.45 (d, 1H), 9.9 (s, 1H); m/z 571.

Workup

  1. stirringThe reaction was stirred at 0° C. for 10 minutes
  2. customThe supernatant water layer was decanted off
  3. washthe residual oil was washed with more water
  4. customthis was decanted off
  5. customthe oil partitioned between EtOAc (100 ml) and water (50 ml)
  6. customThe layers were separated
  7. washthe organic layer washed with water (50 ml)
  8. customdried
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-e9c67577fb3347b9b3361edc69d794bd
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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