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

HRID 2364093
Notes
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Reaction equation

HRID 2364093 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].O=[C:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[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+]>CCCCCC.CO.CCOC(C)=O.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:17]3([CH2:18][CH2:19][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:21][CH2:22]3)[NH:1][C:2]=2[CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

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 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 667430133-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide

Product 1

HCID 68074185
tert-butyl [6'-(5-methyl-1H-pyrazol-4-yl)-4'-oxo-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4-yl]carbamate

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 31374DimethylacetamideSolventHCID 21584119Ethylacetate methanolSolvent

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), tert-butyl (4-oxocyclohexyl)carbamate (320 mg, 1.50 mmol), MgSO4 (120 mg, 1.00 mmol), CSA (11.6 mg, 0.05 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 residue obtained was dissolved with small amount of MeOH/EtOAc and added dropwise to a stirred solution of hexane (100 mL). The precipitate was collected by filtration to afford the title compound (122 mg, 58%, a mixture of 11:9 cis/trans isomers, absolute structure not determined) as 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 residue obtained
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a18a7a35cc91476dbfff8185b58e21a8
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