Ethyl piperidine-2-carboxylate → HCID 53865111, compound

HRID 2268606Notes

Reaction equation

HRID 2268606 reaction equation
[C:1]([O:5][C:6]([N:8]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:15](O)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[NH:34]1[CH2:44][CH2:43][CH2:42][CH2:41][CH:35]1[C:36]([O:38][CH2:39][CH3:40])=[O:37].CCN(C(C)C)C(C)C>ClCCl.CN(C)C=O>[CH2:39]([O:38][C:36]([CH:35]1[CH2:41][CH2:42][CH2:43][CH2:44][N:34]1[C:15](=[O:16])[C:14]1[CH:18]=[C:19]([Cl:21])[CH:20]=[C:12]([O:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:13]=1)=[O:37])[CH3:40]

Participants

7

Reactant 4

HCID 27517Ethyl piperidine-2-carboxylateHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

Product 1

HCID 53865111HCID 53865111, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.12 g) in dichloromethane (4 ml) was added dimethylformamide (0.05 ml) followed by 2M oxalyl chloride solution in dichloromethane (0.183 ml). The resultant solution was stirred at room temperature for 1 h, and then ethyl pipecolinate (0.096 g) followed by DIPEA (0.160 ml) were added. After 18 h, the reaction mixture was concentrated under reduced pressure and the residue was subjected to preparative hplc. The title compound (0.165 g) was obtained as a colourless oil by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

  1. additionwere added
  2. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc2c2f7cc4cd428b836cbbd646c26df2
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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