Potassium tert-butoxide → HCID 178499450, compound

HRID 1852482Notes

Reaction equation

HRID 1852482 reaction equation
[C:1]([C:4]1[C:5]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:28][CH:27]=2)=[N:6][N:7](C2(CC#N)CCN(C(OC(C)(C)C)=O)CC2)[CH:8]=1)(=[O:3])[NH2:2].CC([O-])(C)C.[K+]>C1COCC1.[NH4+].[Cl-]>[C:1]([C:4]1[C:5]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:30][CH:31]=2)=[N:6][NH:7][CH:8]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86729389tert-butyl 4-(4-carbamoyl-3-{[4-(2-methoxy-2-oxoethyl)phenyl]amino}-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidine-1-carboxylate

Product 1

HCID 178499450HCID 178499450, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-Butyl 4-(4-carbamoyl-3-{[4-(2-methoxy-2-oxoethyl)phenyl]amino}-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidine-1-carboxylate (226 mg, 0.46 mmol) in THF (2.3 mL) at 0° C. was added KOtBu (0.68 mL, 0.68 mmol, 1.0M in THF), and the mixture was stirred at 0° C. for 20 minutes, then ambient temperature for 20 minutes. The mixture was diluted with saturated aqueous NH4Cl, and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. Et2O (5 mL) was added to the resulting oily residue and a solid precipitated out. This solid was collected by decant, and washed with Et2O to afford the title compound. LRMS (ESI) calc'd for C13H15N4O3 [M+H]+: 275. Found: 275.

Workup

  1. waitambient temperature for 20 minutes
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. additionEt2O (5 mL) was added to the resulting oily residue
  7. customa solid precipitated out
  8. customThis solid was collected
  9. customby decant
  10. washwashed with Et2O

Sources & evidence

ORD record
ord-8ed422a1a7504791a16650a0c06fc589
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

Loading…