1,1'-Carbonyldiimidazole → HCID 59850137, compound

HRID 2064122Notes

Reaction equation

HRID 2064122 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Cl:9])=[CH:4][C:3]=1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25]>O1CCCC1>[Cl:9][C:5]1[C:6]([F:8])=[CH:7][C:2]2[NH:1][C:24](=[O:25])[N:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59850166HCID 59850166, compound

Product 1

HCID 59850137HCID 59850137, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1,1-Dimethylethyl 4-[(2-amino-5-chloro-4-fluorophenyl)amino]-1-piperidinecarboxylate (D3) (0.87 mmol, 300 mg) was dissolved in 5 ml of tetrahydrofuran and carbonyldiimidazole (1,1′-(oxomethanediyl)bis-1H-imidazole) (3 eq., 2.6 mmol, 440 mg) was added at room temperature; the mixture was refluxed at 50° C. overnight. The mixture was cooled to room temperature, THF evaporated and it was diluted in ethyl acetate/H2O/NaHCO3 (saturated solution); the two layers were separated and the aqueous phase was extracted with ethyl acetate (2×); the organic phases were combined and washed with water and NaHCO3 (saturated solution), they were dried over Na2SO4, filtered and the solvent was evaporated to afford the crude compound that was purified by chromatography (methanol-NH3-dichloromethane) to yield the title compound, 170 mg 53%, M+−H=368.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customTHF evaporated
  3. additionit was diluted in ethyl acetate/H2O/NaHCO3 (saturated solution)
  4. customthe two layers were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (2×)
  6. washwashed with water and NaHCO3 (saturated solution), they
  7. dry with materialwere dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customto afford the crude compound that
  11. customwas purified by chromatography (methanol-NH3-dichloromethane)

Sources & evidence

ORD record
ord-5129801ea55848d2acca825fb330d1d1
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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