Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 66744049, compound

HRID 2364098Notes

Reaction equation

HRID 2364098 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].[Si:16]([O:23][CH:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O-]S([O-])(=O)=O.[Mg+2]>CC(N(C)C)=O>[Si:16]([O:23][CH:24]1[CH2:25][CH2:26][C:27]2([NH:1][C:2]3[CH:6]=[C:5]([C:7]4[CH:8]=[N:9][NH:10][C:11]=4[CH3:12])[S:4][C:3]=3[C:13](=[O:14])[NH:15]2)[CH2:28][CH2:29]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 106094304-(tert-Butyldimethylsilyloxy)cyclohexanoneHCID 667430133-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide

Product 1

HCID 66744049HCID 66744049, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene -2-carboxamide (100 mg, 0.450 mmol), 4-{[tert-butyl(dimethyl) silyl]oxy}cyclohexanone (0.339 mL, 1.35 mmol), CSA (10.5 mg, 0.0450 mmol), MgSO4 (108 mg, 0.900 mmol) in anhydrous DMA (1.5 mL) was stirred at 90° C. for 1 h. The mixture was partitioned between EtOAc (20 mL) and aqueous NaHCO3 (10 mL). The aqueous layer was extracted with EtOAc (5 mL). The combined organic layers were washed with brine (5 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, 30:70 hexane/EtOAc to EtOAc) to give 4-{[tert-butyl(dimethyl)silyl]oxy}-6′-(5-methyl-1H-pyrazol-4-yl)-1′H-spiro[cyclohexane-1,2′-thieno[3,2-d]pyrimidin]-4′(3′H)-one as a pale yellow oil.

Workup

  1. customThe mixture was partitioned between EtOAc (20 mL) and aqueous NaHCO3 (10 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (5 mL)
  3. washThe combined organic layers were washed with brine (5 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (Purif, silica gel, 30:70 hexane/EtOAc to EtOAc)

Sources & evidence

ORD record
ord-5755fbe050fa460d90543f035f5390d8
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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