Cyclopentanol → 12-Chloro-9-cyclopentyloxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide
Reaction equation
[H-].[Na+].[CH:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:11]=[C:12]2[C:21](=[C:22]3[C:27]=1[CH:26]=[CH:25][CH:24]=[N:23]3)[NH:20][S:19](=[O:29])(=[O:28])[C:18]1[C:13]2=[CH:14][C:15](F)=[CH:16][CH:17]=1.OS([O-])(=O)=O.[K+]>CN1C(=O)CCC1>[Cl:9][C:10]1[CH:11]=[C:12]2[C:21](=[C:22]3[C:27]=1[CH:26]=[CH:25][CH:24]=[N:23]3)[NH:20][S:19](=[O:29])(=[O:28])[C:18]1[C:13]2=[CH:14][C:15]([O:8][CH:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)=[CH:16][CH:17]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
NaH (60% in mineral oil; 53 mg, 1.34 mmol) was added to a solution of cyclopentanol (115 mg, 1.34 mmol) in NMP (3 ml) and the mixture was stirred at room temperature for 15 min. 12-chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 503 (150 mg, 0.44 mmol) was added and the mixture was heated at 180 C in a microwave for 2 h. After cooling, the mixture was poured into ice cold water and neutralized using sat aq. KHSO4 solution. The resulting precipitate was collected by filtration and dried. The crude solid was purified by column chromatography with n-hexane/DCM (30:70) as the eluent to give the title compound (23 mg, 20%).
Workup
- temperaturethe mixture was heated at 180 C in a microwave for 2 h
- temperatureAfter cooling
- additionthe mixture was poured into ice cold water
- filtrationThe resulting precipitate was collected by filtration
- customdried
- customThe crude solid was purified by column chromatography with n-hexane/DCM (30:70) as the eluent
Sources & evidence
- ORD record
- ord-c4d73bf1d803409f93ac5ccb34dbfd6c
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102688B2
Reaction notes
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