Isopropyl iodide → HCID 57413951, compound

HRID 532494Notes

Reaction equation

HRID 532494 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[C:14]3[S:21][CH:20]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][C:23]=4[F:32])[C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:8][CH2:7]1.C([O-])([O-])=O.[K+].[K+].I[CH:40]([CH3:42])[CH3:41]>CNC=O.CC(C)=O>[F:32][C:23]1[CH:24]=[C:25]([S:28]([CH3:31])(=[O:29])=[O:30])[CH:26]=[CH:27][C:22]=1[C:19]1[C:15]2[N:16]=[CH:17][N:18]=[C:13]([O:12][CH:9]3[CH2:10][CH2:11][N:6]([C:5]4[N:1]=[N:2][N:3]([CH:40]([CH3:42])[CH3:41])[N:4]=4)[CH2:7][CH2:8]3)[C:14]=2[S:21][CH:20]=1

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 57413952HCID 57413952, compound

Product 1

HCID 57413951HCID 57413951, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 31254N-MethylformamideSolvent

Procedure

700 mg of 4-(1-(2H-tetrazol-5-yl)piperidin-4-yloxy)-7-(2-fluoro-4-methanesulfonyl-phenyl)thieno[3,2-d]pyrimidine obtained in step 94-1 and 41 mf of K2CO3 were added in a mixture of methylformamide and acetone, and 44 μl of 2-iodopropane was dropwise added with stirring. The resulting mixture was stirred at 50° C. for 12 hr, cooled to room temperature and extracted three times with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under a reduced pressure to obtain 51 mg of the title compound.

Workup

  1. additionwas dropwise added
  2. stirringThe resulting mixture was stirred at 50° C. for 12 hr
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-ce57eebea93a47deaa0211933ad697f3
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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