Potassium Carbonate → HCID 53345538, compound

HRID 1465016Notes

Reaction equation

HRID 1465016 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:38])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([NH:22][C:23]([C:25]3[C:29]4[N:30]=[CH:31][N:32]=[C:33]([NH:34][CH:35]5[CH2:37][CH2:36]5)[C:28]=4[S:27][CH:26]=3)=[O:24])[CH:16]=2)=[CH:9][C:8]=1[C:39]([F:42])([F:41])[F:40])(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH3:49][C:50]1[N:51]=[CH:52][NH:53][CH:54]=1>CN(C=O)C.C(OCC)(=O)C>[CH:35]1([NH:34][C:33]2[C:28]3[S:27][CH:26]=[C:25]([C:23]([NH:22][C:17]4[CH:16]=[C:15]([C:14](=[O:38])[NH:13][C:10]5[CH:11]=[CH:12][C:7]([CH2:6][N:53]6[CH:54]=[C:50]([CH3:49])[N:51]=[CH:52]6)=[C:8]([C:39]([F:42])([F:40])[F:41])[CH:9]=5)[CH:20]=[CH:19][C:18]=4[CH3:21])=[O:24])[C:29]=3[N:30]=[CH:31][N:32]=2)[CH2:36][CH2:37]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 53345537HCID 53345537, compoundHCID 178418800HCID 178418800, compound

Product 1

HCID 53345538HCID 53345538, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(3-(4-(Cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxamido)-4-methylbenzamido)-2-(trifluoromethyl)benzyl methanesulfonate (30 mg, 0.048 mmol) was dissolved in DMF (1 mL), K2CO3 (20 mg, 0.145 mmol) and 4-methyl-1H-imidazole (20 mg, 0.242 mmol) were added thereto and stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with brine. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure. The resulting mixture was purified by silica gel chromatography (MeOH/DCM=5/95) to obtain the title compound (23 mg, 78% yield).

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting mixture was purified by silica gel chromatography (MeOH/DCM=5/95)

Sources & evidence

ORD record
ord-882f2ba0331249c4ad1cefa0450858e5
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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