Potassium Carbonate → HCID 56592600, compound

HRID 1616091Notes

Reaction equation

HRID 1616091 reaction equation
N1([O:10][C:11]2[C:12]3[O:19][CH:18]=[C:17]([CH:20]4[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]4)[C:13]=3[N:14]=[CH:15][N:16]=2)C2C=CC=CC=2N=N1.[CH3:33][S:34]([C:37]1[CH:42]=[CH:41][C:40](O)=[CH:39][CH:38]=1)(=[O:36])=[O:35].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:33][S:34]([C:37]1[CH:42]=[CH:41][C:40]([O:10][C:11]2[C:12]3[O:19][CH:18]=[C:17]([CH:20]4[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:24][CH2:25]4)[C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:39][CH:38]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1233504-(Methylsulfonyl)phenolHCID 86681871HCID 86681871, compound

Product 1

HCID 56592600HCID 56592600, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an argon atmosphere, the tert-butyl 4-{4-[(1H-benzo[d][1,2,3]triazol-1-yl)oxy]furo[3,2-d]pyrimidin-7-yl}piperidine-1-carboxylate (10 mg, 0.023 mmol) obtained in Step 7 of Example 1 and 4-(methylsulfonyl)phenol (4 mg, 0.023 mmol) were dissolved in anhydrous N,N-dimethyl formaldehyde (0.5 mL), potassium carbonate (5 mg, 0.035 mmol) was added, stirring was conducted at room temperature for 2 hours, water was added, followed by extraction with toluene. The organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and the obtained residue was purified by silica gel preparative thin layer chromatography (hexane:ethyl acetate=1:2) to give the titled compound (10 mg, 89%) as a pale yellow solid.

Workup

  1. extractionfollowed by extraction with toluene
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customthe obtained residue was purified by silica gel preparative thin layer chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-9af1eafda5a14d339ca6289bdd0f58a9
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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