Potassium Carbonate → HCID 24936355, compound

HRID 2365207Notes

Reaction equation

HRID 2365207 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2S(C2C=CC(C)=CC=2)(=O)=O)=[C:4]([C:21]2[N:22]=[C:23]([N:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)[C:24]3[S:29][C:28]([CH2:30]OS(C4C=CC(C)=CC=4)(=O)=O)=[CH:27][C:25]=3[N:26]=2)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:54][C@H:55]1[CH2:60][NH:59][CH2:58][C@@H:57]([CH3:61])[NH:56]1.[OH-].[Na+].[Cl-].[NH4+]>CN(C=O)C.C(Cl)Cl.O>[CH3:54][C@H:55]1[NH:56][C@@H:57]([CH3:61])[CH2:58][N:59]([CH2:30][C:28]2[S:29][C:24]3[C:23]([N:42]4[CH2:43][CH2:44][O:45][CH2:46][CH2:47]4)=[N:22][C:21]([C:4]4[CH:3]=[C:2]([F:1])[CH:10]=[C:9]5[C:5]=4[CH:6]=[CH:7][NH:8]5)=[N:26][C:25]=3[CH:27]=2)[CH2:60]1

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 58117092HCID 58117092, compound

Product 1

HCID 24936355HCID 24936355, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of toluene-4-sulfonic acid 2-[6-fluoro-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl ester (100 mg, 0.144 mmol) in DMF (1 mL) were added potassium carbonate (100 mg, 0.724 mmol) and (cis)-2,6-dimethyl-piperazine (33 mg, 0.289 mmol). The reaction mixture was stirred at RT for 2 h before water and DCM were added. The phases were separated using a hydrophobic frit and the organic phase was concentrated in vacuo. The resultant residue was dissolved in dioxane (1 mL) and IMS (1 mL), and an aqueous solution of NaOH (12 M, 1 mL, 12 mmol) was added. The mixture was stirred at RT for 3 h before a sat. aqueous solution of ammonium chloride and DCM were added.

Workup

  1. additionwere added
  2. customThe phases were separated
  3. concentrationthe organic phase was concentrated in vacuo
  4. dissolutionThe resultant residue was dissolved in dioxane (1 mL)
  5. additionwere added

Sources & evidence

ORD record
ord-b531dc505b1a4dddac6a9ba6115d0f1d
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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