Aniline → HCID 22005505, compound

HRID 362619Notes

Reaction equation

HRID 362619 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([N:23]2[C:27]([C:28]3[CH:33]=[CH:32][N:31]=[C:30](Cl)[CH:29]=3)=[C:26]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[N:25]=[CH:24]2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[OH-].[Na+]>CC(N(C)C)=O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([N:23]2[C:27]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]([NH:3][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH:29]=3)=[C:26]([C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[N:25]=[CH:24]2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 22005501HCID 22005501, compound

Product 1

HCID 22005505HCID 22005505, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of NaH (130 mg, 3.3 mmol) in DMA (2 mL) was added aniline (0.58 mL, 6.1 mmol) and stirred until bubling ceased. To this solution was added 1-(1-t-butoxycarbonyl-4-piperidinyl)-4-(4-fluorophenyl)-5-(2-chloro-4-pyridinyl)imidazole (0.30 g, 0.66 mmol) and the resulting solution was heated at 120° C. until no evidence of starting material was observed by mass spectroscopy (1-3 days). To the cooled reaction mixture 1M NaOH was added and the resulting mixture extracted three times with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and the filtrate concentrated under reduced pressure to afford a yellow residue which was chromatographed with 50-80% EtOAc/hexanes. The resulting solid was triturated with Et2O to give the title compound as a light yellow solid; yield 180 mg (53%): ESMS m/z=514(M+ +H).

Workup

  1. customwas observed by mass spectroscopy (1-3 days)
  2. additionwas added
  3. extractionthe resulting mixture extracted three times with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customto afford a yellow residue which
  9. customwas chromatographed with 50-80% EtOAc/hexanes
  10. customThe resulting solid was triturated with Et2O

Sources & evidence

ORD record
ord-064aedc5de9c4413a9eab4ebf8d7053f
Source dataset
uspto-grants-1999_02
Patent number
US05869660

Reaction notes

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