1,1'-Carbonyldiimidazole → HCID 59683283, compound

HRID 447778Notes

Reaction equation

HRID 447778 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:11][CH2:10]2)=[CH:4][C:3]=1[NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C1N=CN([C:31](N2C=NC=C2)=[O:32])C=1>O1CCCC1>[CH:9]1([C:5]2[CH:6]=[C:7]([F:8])[C:2]3[NH:1][C:31](=[O:32])[N:12]([CH:13]4[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]4)[C:3]=3[CH:4]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 596832651,1-Dimethylethyl 4-[(2-amino-5-cyclopropyl-3-fluorophenyl)amino]-1-piperidinecarboxylate

Product 1

HCID 59683283HCID 59683283, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1-Dimethylethyl 4-[(2-amino-5-cyclopropyl-3-fluorophenyl)amino]-1-piperidine-carboxylate (D27, 0.80 mmol, 280 mg) was dissolved in 4 ml of tetrahydrofuran and CDI (1,1′-(oxomethanediyl)bis-1H-imidazole) (2.5 eq., 2.0 mmol, 0.33 g) at room temperature and the mixture was stirred at 50° C. for one overnight under argon. Extra CDI (1 eq., 0.13 g, 0.80 mmol) was added and the mixture was refluxed for two extra hours. The mixture was cooled to room temperature and the solvent was evaporated to afford the crude compound which was purified by chromatography (ethyl acetate (50)-n-hexane (50)) to yield the title compound, 102 mg, 36%, M−−H=374.

Workup

  1. temperaturethe mixture was refluxed for two extra hours
  2. customthe solvent was evaporated
  3. customto afford the crude compound which
  4. customwas purified by chromatography (ethyl acetate (50)-n-hexane (50))

Sources & evidence

ORD record
ord-31e4022220ac4886b885c3cebeea2491
Source dataset
uspto-grants-2013_07
Patent number
US08481566B2

Reaction notes

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