Pyridine → HCID 57920212, compound

HRID 2098376Notes

Reaction equation

HRID 2098376 reaction equation
[CH3:1][C:2]1([C:15](=[O:28])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[O:27][CH:26]=[N:25][CH:24]=3)[CH:18]=2)[CH2:7][CH2:6][N:5]([C:8](OC(C)(C)C)=O)[CH2:4][CH2:3]1.C(OC([N:36]1[CH2:41]CC(C)(C(O)=O)CC1)=O)(C)(C)C.[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(Cl)(=O)C(Cl)=O.O1C(C2C=C(C=CC=2)N)=C[N:60]=C1>ClCCCl.CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1([C:15]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[O:27][CH:26]=[N:25][CH:24]=3)[CH:18]=2)=[O:28])[CH2:3][CH2:4][N:5]([C:8]2[C:50]3[C:48]([CH3:49])=[CH:47][NH:46][C:51]=3[N:60]=[CH:41][N:36]=2)[CH2:6][CH2:7]1

Participants

9

Reactant 5

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 27392893-(1,3-Oxazol-5-yl)anilineHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acidHCID 67036759Tert-butyl 4-methyl-4-(3-(oxazol-5-yl)phenylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 57920212HCID 57920212, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Preparation of tert-butyl 4-methyl-4-(3-(oxazol-5-yl)phenylcarbamoyl)piperidine-1-carboxylate. 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-dfa20defd3cc4051b90c1b015fe29612
Source dataset
uspto-grants-2013_05
Patent number
US08450332B2

Reaction notes

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