4-Toluenesulfonyl chloride → 4-tert.-butyl-N-{6-[2-(toluenesulfonyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamide
Reaction equation
[CH2:1]1CCN2C(=NCCC2)CC1.[NH2:12][CH2:13][CH2:14][O:15][C:16]1[N:21]=[CH:20][N:19]=[C:18]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:17]=1[C:36]1[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=1.[S:43](Cl)([C:46]1[CH:52]=[CH:51][C:49](C)=[CH:48][CH:47]=1)(=[O:45])=[O:44]>>[C:32]([C:29]1[CH:30]=[CH:31][C:26]([S:23]([NH:22][C:18]2[C:17]([C:36]3[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=3)=[C:16]([O:15][CH2:14][CH2:13][NH:12][S:43]([C:46]3[C:47]([CH3:1])=[CH:48][CH:49]=[CH:51][CH:52]=3)(=[O:44])=[O:45])[N:21]=[CH:20][N:19]=2)(=[O:24])=[O:25])=[CH:27][CH:28]=1)([CH3:35])([CH3:34])[CH3:33]Participants
4
Reactant 3
Product 1
Procedure
According to Example 4a) with DBU instead of Hünig's base, 200 mg N-[6-(2-amino-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-4-tert.-butyl-benzenesulfonamide was reacted with tosylchloride to give 147 mg 4-tert.-butyl-N-{6-[2-(toluenesulfonyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamide. LC-MS: tR=5.85 min, [M−1]−=593.50.
Sources & evidence
- ORD record
- ord-65ebfb7f0a474acea8718517744c0eb5
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06596719B1
Reaction notes
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