Dichloromethane → 4-chloro-N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-benzenesulphonamide
Reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:13]=[C:12]([Cl:14])[N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(Cl)Cl.C(N(CC)CC)C.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>O>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:1][CH2:2][CH2:3][NH:4][C:5]2[N:13]=[C:12]([Cl:14])[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:39])=[O:38])=[CH:33][CH:32]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The operation is carried out as in Stage 1 of Example 10 starting from 280 mg of the product obtained in Stage 1 of Example 7, 4 ml of methylene chloride, 0.2 ml of triethylamine and 255 mg of 4-chlorobenzenesulphonic acid chloride in place of the 4-methyl-benzenesulphonic acid chloride then the reaction medium is agitated at ambient temperature for 30 minutes. Then 2 ml of water is added, followed by extracting with 3×5 ml of methylene chloride, washing with 5 ml of saturated sodium chloride, drying, evaporating, impasting in 5 ml of ether then in 5 ml of pentane, separating, and drying. After chromatography on silica eluting with methylene chloride/CH3CN in a proportion of 70/30, 350 mg of expected product is obtained in the form of a beige solid.
Workup
- extractionby extracting with 3×5 ml of methylene chloride
- washwashing with 5 ml of saturated sodium chloride
- customdrying
- customevaporating
- customin 5 ml of pentane, separating
- customdrying
Sources & evidence
- ORD record
- ord-609898ff91604a8f95fdf71c1e0f58f5
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07122669B1
Reaction notes
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