Pyridine → HCID 67036759, compound

HRID 216039Notes

Reaction equation

HRID 216039 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:17])([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[O:30]1[C:34]([C:35]2[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=2)[NH2:38])=[CH:33][N:32]=[CH:31]1>ClCCCl.CN(C=O)C.C(OCC)(=O)C>[CH3:17][C:11]1([C:14](=[O:16])[NH:38][C:37]2[CH:39]=[CH:40][CH:41]=[C:35]([C:34]3[O:30][CH:31]=[N:32][CH:33]=3)[CH:36]=2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 27392893-(1,3-Oxazol-5-yl)anilineHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acid

Product 1

HCID 67036759HCID 67036759, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (61.3 mg, 0.252 mmol) and pyridine (79.7 mg, 0.08 mL, 1.01 mmol) in 1,2-dichloroethane (2 mL) at 0° C. was added DMF (1-2 drops) followed by oxalyl chloride (31.9 mg, 0.022 mL, 0.252 mmol). The reaction was stirred for 0.5 hour, and 3-(oxazol-5-yl)aniline (40.4 mg, 0.252 mmol) was added. The reaction was allowed to stir for another 1.5 hours. The mixture was diluted with ethyl acetate (10 mL), and the organics were washed with 0.1 N HCl (2×10 mL), brine (4 mL), dried over MgSO4, filtered, and concentrated to give the title compound, which was used in the next step without further purification. MS (ES+) [M+H]+=386.2.

Workup

  1. stirringto stir for another 1.5 hours
  2. washthe organics were washed with 0.1 N HCl (2×10 mL), brine (4 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5dddd8738fb7483dadad9cbca615ce48
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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