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p-Toluenesulfonic acid monohydrate → 1-Cyclohexyl-5-[2-methoxy-4-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)phenyl]-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 915949
Notes
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Reaction equation

HRID 915949 reaction equation
[CH:1]1([N:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:22]=[CH:21][C:20]([C:23]5(O)[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]5)=[CH:19][C:18]=4[O:31][CH3:32])=[N:11][C:10]=3[C:9]([CH3:33])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1]1([N:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:22]=[CH:21][C:20]([C:23]5[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH:24]=5)=[CH:19][C:18]=4[O:31][CH3:32])=[N:11][C:10]=3[C:9]([CH3:33])=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 1360059331-Cyclohexyl-5-[4-(4-hydroxy-1-methyl-4-piperidinyl)-2-methoxyphenyl]-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1360058441-Cyclohexyl-5-[2-methoxy-4-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)phenyl]-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 51.4%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To a 10 ml toluene solution of 160 mg (0.35 mmol) of the compound obtained in Example 122, 135 mg (0.71 mmol) of p-toluenesulfonic acid monohydrate was added, and the mixture was heated under reflux for 22 hours with the use of a Dean-Stark dehydrator. The reaction mixture was returned to room temperature, and washed with a saturated aqueous solution of sodium hydrogen carbonate. The system was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) to obtain 78 mg (51%) of the captioned compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 22 hours with the use of a Dean-Stark dehydrator
  3. customwas returned to room temperature
  4. washwashed with a saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materialThe system was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-bbd558c4743d48ef97d781097fdb13dd
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07268128B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes