Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 68074178, compound

HRID 2364080Notes

Reaction equation

HRID 2364080 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[C:8]([CH3:12])=[N:9][NH:10][CH:11]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].O=[C:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][CH2:18]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>[CH3:12][C:8]1[NH:9][N:10]=[CH:11][C:7]=1[C:5]1[S:4][C:3]2[C:13](=[O:14])[NH:15][C:17]3([CH2:18][CH2:19][CH:20]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:21][CH2:22]3)[NH:1][C:2]=2[CH:6]=1

Participants

7

Reactant 5

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 14615292Benzyl (4-oxocyclohexyl)carbamateHCID 178434532HCID 178434532, compound

Product 1

HCID 68074178HCID 68074178, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-amino-5-(3-methyl-1H-pyrazol-4-yl) thiophene-2-carboxamide (111 mg, 0.50 mmol), benzyl (4-oxocyclohexyl)carbamate (495 mg, 2.00 mmol), MgSO4 (120 mg, 1.00 mmol), CSA (11.61 mg, 0.050 mmol) and DMA (3 mL) was stirred at 100° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc, and the extract was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to EtOAc then to 80:20 EtOAc/MeOH). The obtained residue was triturated with 2-propanol-EtOAc, and the precipitate was collected by filtration to afford the title compound (58.4 mg, 26%, a mixture of 4:1 cis/trans isomers, absolute structure not determined) as a yellow solid:

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe extract was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (Purif, silica gel, hexane to EtOAc
  6. customThe obtained residue was triturated with 2-propanol-EtOAc
  7. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-69258935c43b41a5a828835fae419b7c
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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