Water → HCID 178495715, compound

HRID 548768Notes

Reaction equation

HRID 548768 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:14]([NH:16][C:17]2[CH:21]=[CH:20][N:19](C(OC(C)(C)C)=O)[N:18]=2)=[O:15])[CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=1.F[C:30]1[CH:35]=[C:34](F)[C:33]([F:37])=[CH:32][C:31]=1[S:38]([CH:41]1[CH2:45][CH2:44][O:43]C1=O)(=[O:40])=[O:39].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:37][C:33]1[C:34]([O:1][C:2]2[CH:3]=[C:4]([CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=2)[C:14]([NH:16][C:17]2[CH:21]=[CH:20][NH:19][N:18]=2)=[O:15])=[CH:35][C:30]2[O:43][CH2:44][CH2:45][CH2:41][S:38](=[O:40])(=[O:39])[C:31]=2[CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 576631723-[(2,4,5-trifluorophenyl)sulfonyl]dihydrofuran-2(3H)-oneHCID 59127185tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

Product 1

HCID 178495715HCID 178495715, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,1-Dimethylethyl 3-{[(3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}phenyl) carbonyl]amino}-1H-pyrazole-1-carboxylate (145 mg, 0.5 mmol), 3-[(2,4,5-trifluorophenyl)sulfonyl]dihydrofuran-2(3H)-one (140 mg, 0.5 mmol) and potassium carbonate (138 mg, 2 mmol) in acetonitrile (4 mL) were heated at 130° C. for 1 hour then 160° C. for a further 1 hour in a microwave reactor. Water was added to the reaction mixture and the phases separated. The aqueous phase was extracted with ethyl acetate (3×20 mL), and the combined organics washed with 1M hydrochloric acid, a saturated sodium bicarbonate solution, brine, dried (MgSO4), filtered and evaporated. The residue was chromatographed on alumina, eluting with 0-10% methanol in DCM, to give the desired compound as a white solid (58 mg).

Workup

  1. customthe phases separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×20 mL)
  3. washthe combined organics washed with 1M hydrochloric acid
  4. dry with materiala saturated sodium bicarbonate solution, brine, dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on alumina
  8. washeluting with 0-10% methanol in DCM

Sources & evidence

ORD record
ord-8ccc8d13c7724b589a92cb1582f18f83
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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