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Methanol → 4-Methoxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline

HRID 238225
Notes
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Reaction equation

HRID 238225 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH:12]([N:14]2[CH2:19][CH2:18][N:17]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:16][CH2:15]2)[CH3:13])[N:3]=1.[CH3:31][OH:32]>C1COCC1>[CH3:31][O:32][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH:12]([N:14]2[CH2:19][CH2:18][N:17]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:16][CH2:15]2)[CH3:13])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 887MethanolHCID 599934264-Chloro-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline

Product 1

HCID 167387094-Methoxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazolineYield 11.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In a test tube containing of 4-Chloro-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline (38.0 mg, 0.089 mmol) in THF (2 ml) was added MeOH (280.0 mg, 8.9 mmol). The reaction was heated at 60° C. for 0.5 hour. The solution was concentrated under reduced pressure. The residue was partitioned between water (2 ml) and dichloromethane (5 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The solvent was removed under vacuum. The resulting residue was re-dissolvent in MeOH (2 ml) and purified by HPLC (Gilson-215, 0.035% TFA in acetonitrile and 0.05% water as mobile phase). The product was collected and dried under reduced pressure to give 4-Methoxy-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-quinazoline (Yield 4.43 mg, 11.13%). MS m/z calc. 442.17, found (ESI); 443.4 (M+1)+. Retention time 2.40 minutes.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customThe residue was partitioned between water (2 ml) and dichloromethane (5 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe solvent was removed under vacuum
  7. dissolutionThe resulting residue was re-dissolvent in MeOH (2 ml)
  8. custompurified by HPLC (Gilson-215, 0.035% TFA in acetonitrile and 0.05% water as mobile phase)
  9. customThe product was collected
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-4dc0380d96824feaa98d2fb8893dec30
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642609B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes