Potassium Carbonate → HCID 58542358, compound

HRID 1951894Notes

Reaction equation

HRID 1951894 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[N:15]3[C:11]([S:12][C:13]([C:19]([N:21]4[CH2:41][C@H:40]([F:42])[CH2:39][C@H:22]4[C:23]([N:25]4[CH2:32][C:29]5([CH2:31][CH2:30]5)[N:28](C(=O)C(F)(F)F)[CH2:27][CH2:26]4)=[O:24])=[O:20])=[C:14]3[CH:16]([CH3:18])[CH3:17])=[N:10][C@:9]2([C:44]2[CH:45]=[N:46][C:47]([Cl:50])=[CH:48][CH:49]=2)[CH3:43])=[CH:4][C:3]=1[F:51].C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[N:15]3[C:11]([S:12][C:13]([C:19]([N:21]4[CH2:41][C@H:40]([F:42])[CH2:39][C@H:22]4[C:23]([N:25]4[CH2:32][C:29]5([CH2:30][CH2:31]5)[NH:28][CH2:27][CH2:26]4)=[O:24])=[O:20])=[C:14]3[CH:16]([CH3:17])[CH3:18])=[N:10][C@:9]2([C:44]2[CH:45]=[N:46][C:47]([Cl:50])=[CH:48][CH:49]=2)[CH3:43])=[CH:4][C:3]=1[F:51]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 58542416HCID 58542416, compound

Product 1

HCID 58542358HCID 58542358, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

The compound (390 mg, 0.51 mmol) obtained in Step 1 above was dissolved in 10% aqueous methanol (8 ml), potassium carbonate (400 mg, 2.89 mmol) was added and the resulting mixture was stirred under heating at 40° C. for 2 hours. The solvent was concentrated under reduced pressure and then the residue obtained was diluted with ethyl acetate, washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [chloroform:methanol=15:1 (v/v)] to give the title compound (190 mg, 55%) as a colorless solid.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customthe residue obtained
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography [chloroform:methanol=15:1 (v/v)]

Sources & evidence

ORD record
ord-e3ac3b5b86e749de8ec324e74e02386f
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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