p-Toluenesulfonic acid monohydrate → HCID 178497015, compound

HRID 270980Notes

Reaction equation

CO[C:3](=[O:18])[CH:4]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=O.[CH3:19][O:20][C:21]([C:23]1[CH:27]=[C:26]([NH2:28])[NH:25][N:24]=1)=[O:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1>[CH3:19][O:20][C:21]([C:23]1[CH:27]=[C:26]2[NH:28][C:5]([C:7]3[O:8][CH:9]=[CH:10][CH:11]=3)=[C:4]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[C:3](=[O:18])[N:25]2[N:24]=1)=[O:22]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1.1 g (4.4 mmol) of 2-cyclohexyl-3-furan-2-yl-3-oxo-propionic acid methyl ester, 0.592 g (4.2 mmol) of 5-amino-1H-pyrazole-3-carboxylic acid methyl ester, 76 mg (0.4 mmol, 10 mol %) of p-toluenesulfonic acid monohydrate (PTSA), and 50 mL of chlorobenzene was heated at 120° C. overnight. The reaction mixture was then concentrated to a residue which was chromatographed on silica gel (7% methanol in dichloromethane) to afford 0.46 g (32% yield) of desired 6-cyclohexyl-5-furan-2-yl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid methyl ester as indicated by 1H NMR; LC-MS—calcd for C18H19N3O4 [M++H]+: 342.14, found: 342.3.

Workup

concentrationThe reaction mixture was then concentrated to a residue which
customwas chromatographed on silica gel (7% methanol in dichloromethane)

Sources & evidence

ORD record: ord-88a77aafbfdc4fc7bb565ce92bd4724d
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449488B2

Reaction notes

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