1,1'-Carbonyldiimidazole → HCID 59850145, compound

HRID 2064163Notes

Reaction equation

HRID 2064163 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([CH3:12])=[CH:4][C:3]=1[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C1N=CN([C:32](N2C=NC=C2)=[O:33])C=1>O1CCCC1>[CH3:12][C:5]1[C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]2[NH:1][C:32](=[O:33])[N:13]([CH:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]3)[C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 598501931,1-Dimethylethyl 4-{[2-amino-5-methyl-4-(trifluoromethyl)phenyl]amino}-1-piperidinecarboxylate

Product 1

HCID 59850145HCID 59850145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

1,1-Dimethylethyl 4-{[2-amino-5-methyl-4-(trifluoromethyl)phenyl]amino}-1-piperidine-carboxylate (D58) (2.92 mmol, 1.1 g) was dissolved in 5 ml of tetrahydrofuran and CDI (1,1′-(oxomethanediyl)bis-1H-imidazole) (1.5 eq., 4.4 mmol, 0.71 g) was added at room temperature; the mixture was stirred at 50-60° C. overnight. The mixture was cooled to room temperature and it was partitioned in ethyl acetate/H2O; the two layers were separated and the aqueous phase was extracted with ethyl acetate (2×); the organic phases were combined and washed with citric acid solution (10% aqueous), brine and they were dried over Na2SO4, filtered and the solvent was evaporated to afford the crude compound that was purified by chromatography (ethyl acetate-n-hexane)) to yield the title compound, 900 mg, 81%, M+−H=398.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customit was partitioned in ethyl acetate/H2O
  3. customthe two layers were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (2×)
  5. washwashed with citric acid solution (10% aqueous), brine and they
  6. dry with materialwere dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customto afford the crude compound that
  10. customwas purified by chromatography (ethyl acetate-n-hexane))

Sources & evidence

ORD record
ord-dbd91615226e4a2d857ad64735f89156
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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