Potassium Carbonate → HCID 89752097, compound

HRID 1842613Notes

Reaction equation

HRID 1842613 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C:10]([F:15])([F:14])[C@@H:9]1[NH:16][C:17]([C:19]1[S:20][C:21]([CH2:34][CH3:35])=[C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[C:31]([OH:33])[CH:30]=[N:29][C:28]=23)[CH:23]=1)=[O:18])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)S(O[CH2:43][C:44]([F:47])([F:46])[F:45])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C:10]([F:14])([F:15])[C@@H:9]1[NH:16][C:17]([C:19]1[S:20][C:21]([CH2:34][CH3:35])=[C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[C:31]([O:33][CH2:43][C:44]([F:47])([F:46])[F:45])[CH:30]=[N:29][C:28]=23)[CH:23]=1)=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 89750984HCID 89750984, compound

Product 1

HCID 89752097HCID 89752097, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

tert-Butyl[(1R,2R)-2-({[5-ethyl-4-(6-hydroxypyrazolo[1,5-a]pyrimidin-3-yl)thiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexyl]carbamate (81.0 mg, 0.155 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (40.3 mg, 0.173 mmol), and potassium carbonate (27.9 mg, 0.202 mmol) were placed in a sealed tube and heated to 40° C. for 6 h. The reaction mixture was cooled to room temperature and diluted with dichloromethane. The organic layer was washed with 1N NaOH (aq) once and 1N HCl (aq) twice. Water was added and the product extracted 3× with dichloromethane. The organic layers were combined, dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified via column chromatography (0-100% EtOAc/Hex) to give the title compound (34.0 mg, 0.056 mmol). LRMS (APCI) calc'd for (C26H30F5N5O4S) [M+H]+, 604.2; found 604.0.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with 1N NaOH (aq) once
  3. additionWater was added
  4. extractionthe product extracted 3× with dichloromethane
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified via column chromatography (0-100% EtOAc/Hex)

Sources & evidence

ORD record
ord-1ca52a0280524b219adbc0fc001ce1fd
Source dataset
uspto-grants-2015_02
Patent number
US08946237B2

Reaction notes

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