Potassium Carbonate → HCID 73602994, compound

HRID 1915957Notes

Reaction equation

HRID 1915957 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][C:11]([NH:40]C(=O)OC(C)(C)C)=[C:12]([C:14](=[O:39])[NH:15][C:16]2[CH:17]=[N:18][N:19]([CH3:38])[C:20]=2[N:21]2[CH2:30][CH2:29][C@@H:28]([NH:31]C(=O)C(F)(F)F)[C:24]3([CH2:27][CH2:26][O:25]3)[CH2:23][CH2:22]2)[N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:40][C:11]1[S:10][C:9]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=2[F:8])=[N:13][C:12]=1[C:14]([NH:15][C:16]1[CH:17]=[N:18][N:19]([CH3:38])[C:20]=1[N:21]1[CH2:22][CH2:23][C:24]2([O:25][CH2:26][CH2:27]2)[CH:28]([NH2:31])[CH2:29][CH2:30]1)=[O:39]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86680155HCID 86680155, compound

Product 1

HCID 73602994HCID 73602994, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl N-[2-(2,6-difluorophenyl)-4-[[1-methyl-5-[(10R)-10-[(2,2,2-trifluoroacetyl)amino]-3-oxa-7-azaspiro[3.6]decan-7-yl]pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate (30 mg, 0.044 mmol) in methanol (2 mL) and water (2 mL) was added potassium carbonate (67 mg, 0.48 mmol). The mixture was heated at 65° C. for 8 h. After cooling to room temperature, the reaction mixture was diluted with water and extracted with EA 3×. Combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was stirred with DCM (4 mL) and TFA (2 mL) for 20 min and concentrated under reduced pressure, basified with saturated NaHCO3, and extracted with ethyl acetate (3×). The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure and the residue purified by preparative HPLC to afford 510. LCMS (ES+) m/z 490 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EA 3×
  3. dry with materialCombined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationconcentrated under reduced pressure
  7. extractionextracted with ethyl acetate (3×)
  8. dry with materialThe combined organic layers were dried over MgSO4
  9. customthe solvent removed under reduced pressure
  10. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-bf41b47fead14d69aa51761d6fb4c235
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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