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Cyclopentanol → 12-Chloro-9-cyclopentyloxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513769
Notes
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Reaction equation

HRID 513769 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 6818318212-Chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Product 1

HCID 6016476112-Chloro-9-cyclopentyloxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 20%

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

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

  1. temperaturethe mixture was heated at 180 C in a microwave for 2 h
  2. temperatureAfter cooling
  3. additionthe mixture was poured into ice cold water
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried
  6. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09102688B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes