Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 66744240, compound

HRID 2364106Notes

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].[N:16]1[CH:21]=[CH:20][CH:19]=[N:18][C:17]=1[N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O-]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[CH3:12][C:11]1[NH:10][N:9]=[CH:8][C:7]=1[C:5]1[S:4][C:3]2[C:13](=[O:14])[NH:15][C:25]3([CH2:26][CH2:27][N:22]([C:17]4[N:16]=[CH:21][CH:20]=[CH:19][N:18]=4)[CH2:23][CH2:24]3)[NH:1][C:2]=2[CH:6]=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), 1-(2-pyrimidinyl)-piperidin-4-one (266 mg, 1.50 mmol), CSA (11.6 mg, 0.05 mmol), MgSO4 (120 mg, 1.00 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, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, EtOAc to 80:20 EtOAc/MeOH). The obtained yellow solid was triturated with MeOH/EtOAc and collected by filtration to afford the title compound (141 mg, 74%) as a pale yellow solid:

Workup

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

Sources & evidence

ORD record: ord-15ce9f811fc74347a50cec8c6b92d1a1
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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