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Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 2-fluoro-1'-methyl-6'-(5-methyl-1H-pyrazol-4-yl)-1'H-spiro[cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

HRID 2364064
Notes
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Reaction equation

HRID 2364064 reaction equation
[CH3:1][NH:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][NH:11][C:12]=2[CH3:13])[S:5][C:4]=1[C:14]([NH2:16])=[O:15].[F:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=O.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O-]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+]>CCOC(C)=O.CC(N(C)C)=O>[F:17][CH:18]1[C:19]2([N:2]([CH3:1])[C:3]3[CH:7]=[C:6]([C:8]4[CH:9]=[N:10][NH:11][C:12]=4[CH3:13])[S:5][C:4]=3[C:14](=[O:15])[NH:16]2)[CH2:20][CH2:21][CH2:22][CH2:23]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

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 118294042-FluorocyclohexanoneHCID 667434763-(methylamino)-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide

Product 1

HCID 66744050
2-fluoro-1'-methyl-6'-(5-methyl-1H-pyrazol-4-yl)-1'H-spiro[cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one
Yield 58%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(methylamino)-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide (70 mg, 0.30 mmol), 2-fluorocyclohexanone (105 mg, 0.90 mmol), CSA (7.0 mg, 0.030 mmol), MgSO4 (72 mg, 0.60 mmol) and DMA (1 mL) was stirred at 70° C. for 5.5 h. Then, saturated aqueous NaHCO3 and EtOAc were added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, 80:20 hexane/EtOAc to EtOAc), then crystallized from MeOH/EtOAc/hexane to give the title compound (58 mg, 58%) as a yellow solid:

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe organic materials were extracted with EtOAc
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customAfter removal of the solvent at reduced pressure
  8. customthe residue was purified by column chromatography (Purif, silica gel, 80:20 hexane/EtOAc to EtOAc)
  9. customcrystallized from MeOH/EtOAc/hexane

Sources & evidence

ORD record
ord-6641b10d1f81401fbabc6132e94f30ec
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691828B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes