Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 66743246, compound

HRID 2364097Notes

Reaction equation

[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][NH:10][C:11]=2[CH3:12])[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1.[O-]S([O-])(=O)=O.[Mg+2].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[F:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][C:26]3([NH:1][C:2]4[CH:6]=[C:5]([C:7]5[CH:8]=[N:9][NH:10][C:11]=5[CH3:12])[S:4][C:3]=4[C:13](=[O:14])[NH:15]3)[CH2:25][CH2:24]2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene -2-carboxamide (111 mg, 0.50 mmol), N-(4-fluorophenyl)-piperidin-4-one (290 mg, 1.50 mmol), MgSO4 (120 mg, 1.00 mmol), CSA (11.6 mg, 0.05 mmol) and DMA (4 mL) was stirred at 100° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and extracted with 3:1 EtOAc/THF, and the extract was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, EtOAc to 80:20 EtOAc/MeOH). The obtained residue was triturated with EtOAc, and the precipitates were collected by filtration to afford the title compound (102 mg, 51%) as a light yellow solid:

Workup

extractionextracted with 3:1 EtOAc/THF
dry with materialthe extract was dried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (Purif, silica gel, EtOAc to 80:20 EtOAc/MeOH)
customThe obtained residue was triturated with EtOAc
filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record: ord-16714bbe40f24e9da78acd894ea5bac5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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