Dichloromethane → N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-4-methoxy-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.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>O>[Cl:14][C:12]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:5]([NH:4][CH2:3][CH2:2][NH:1][S:38]([C:35]2[CH:34]=[CH:33][C:32]([O:31][CH3:30])=[CH:37][CH:36]=2)(=[O:40])=[O:39])[N:13]=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 248 mg of 4-methoxy-benzenesulphonic acid chloride in place of the 4-methyl-benzenesulphonic acid chloride then agitation is carried out at ambient temperature for approximately one night. 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, 250 mg of expected product is thus obtained in the form of a beige solid.
Workup
- waitthen agitation is carried out at ambient temperature for approximately one night
- 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-b0477b19d1e240099274bd96fda1d6fa
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07122669B1
Reaction notes
Loading…