Potassium Carbonate → HCID 59333777, compound

HRID 1930727Notes

Reaction equation

HRID 1930727 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([NH:21][C:22]([NH2:24])=[NH:23])[CH:12]=[CH:13][C:14]=1[N:15]1[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]1.[F:25][CH2:26][CH:27]([O:30][CH2:31][C:32]([CH:34]1[C:39](=O)[CH2:38][CH2:37][O:36][CH2:35]1)=O)[CH2:28][F:29]>CN(C=O)C>[F:25][CH2:26][CH:27]([O:30][CH2:31][C:32]1[C:34]2[CH2:35][O:36][CH2:37][CH2:38][C:39]=2[N:23]=[C:22]([NH:21][C:11]2[CH:12]=[CH:13][C:14]([N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]3)=[C:9]([O:8][CH3:7])[CH:10]=2)[N:24]=1)[CH2:28][F:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 593337623-(2-(1,3-difluoropropan-2-yloxy)acetyl)dihydro-2H-pyran-4(3H)-oneHCID 178493227HCID 178493227, compound

Product 1

HCID 59333777HCID 59333777, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (222 mg, 1.61 mmol) was added to 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (149 mg, 0.40 mmol) in DMF (1 mL) and set under N2 atmosphere. The DMF (1 mL) solution of 3-(2-(1,3-difluoropropan-2-yloxy)acetyl)dihydro-2H-pyran-4(3H)-one (95 mg, 0.40 mmol) was added dropwise to the reaction mixture and stirred for 16 hours at 50° C. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated and the crude product was purified by silica flash chromatography using a gradient of methanol in dichloromethane (0 to 4%) affording the title compound (120 mg, 67% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe crude product was purified by silica flash chromatography

Sources & evidence

ORD record
ord-5b0f78eaba0a48f2af87e45daab37ef4
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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