Pyridine → tert-butyl 4-(3-(1H-tetrazol-5-yl)phenylcarbamoyl)-4-methylpiperidine-1-carboxylate

HRID 216045Notes

Reaction equation

HRID 216045 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.[NH:30]1[C:34]([C:35]2[CH:36]=[C:37]([NH2:41])[CH:38]=[CH:39][CH:40]=2)=[N:33][N:32]=[N:31]1>ClC(Cl)C.CN(C=O)C>[NH:33]1[C:34]([C:35]2[CH:36]=[C:37]([NH:41][C:14]([C:11]3([CH3:17])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]3)=[O:16])[CH:38]=[CH:39][CH:40]=2)=[N:30][N:31]=[N:32]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acidHCID 178507542HCID 178507542, compound

Product 1

HCID 178451883tert-butyl 4-(3-(1H-tetrazol-5-yl)phenylcarbamoyl)-4-methylpiperidine-1-carboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (100 mg, 0.41 mmol) in dichloroethane (2.0 mL) were added DMF (2 drops) and pyridine (0.13 g, 1.6 mmol), followed by oxalyl chloride (57 mg, 0.45 mmol). The mixture was stirred for 40 minutes, and 3-(1H-tetrazol-5-yl)-phenylamine was added. The mixture was stirred for 2 hours, and a pink precipitate formed. The mixture was filtered, and the filtrate was washed with 1.0 N aq. HCl and brine, dried over MgSO4, and concentrated to give the title compound in 70% yield. MS (ES+) [M+H]+=387.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. customa pink precipitate formed
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed with 1.0 N aq. HCl and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-35e77530188b499c91ddf54ff5d1191f
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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