p-Toluenesulfonic acid monohydrate → HCID 178497016, compound

HRID 270965Notes

Reaction equation

HRID 270965 reaction equation
C[O:2][C:3](=O)[CH:4]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)=O.[CH3:28][O:29][C:30]([C:32]1[CH:36]=[C:35]([NH2:37])[NH:34][N:33]=1)=[O:31].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:28][O:29][C:30]([C:32]1[CH:36]=[C:35]2[NH:37][C:5]([C:7]3[CH:8]=[CH:9][C:10]([O:13][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:11][CH:12]=3)=[C:4]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:3](=[O:2])[N:34]2[N:33]=1)=[O:31]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 588250313-(4-Benzyloxy-phenyl)-2-cyclohexyl-3-oxo-propionic acid methyl esterHCID 178498460HCID 178498460, compound

Product 1

HCID 178497016HCID 178497016, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 274 mg (0.747 mmol) of 3-(4-benzyloxy-phenyl)-2-cyclohexyl-3-oxo-propionic acid methyl ester, 106 mg (0.747 mmol) of 5-amino-1H-pyrazole-3-carboxylic acid methyl ester, 15 mg (10 mol %) of p-toluenesulfonic acid monohydrate (PTSA), and 10 mL of toluene was heated at reflux for 88 h. The reaction mixture was then concentrated to a residue which was chromatographed on silica gel (Biotage; gradient elution 2% to 20% ethyl acetate in dichloromethane) to afford 55 mg (16% yield) of desired 5-(4-benzyloxy-phenyl)-6-cyclohexyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid methyl ester as a solid as indicated by 1H NMR; LC-MS—calcd for C27H27N3O4 [M++H]+: 458.2, found: 458.2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 88 h
  3. concentrationThe reaction mixture was then concentrated to a residue which
  4. customwas chromatographed on silica gel (Biotage; gradient elution 2% to 20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-3b78184750dd49769fe993eab85a9e31
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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