2-Methylpiperidine → HCID 53687742, compound

HRID 2268607Notes

Reaction equation

HRID 2268607 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.[CH3:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][NH:36]1.CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:15]([N:36]2[CH2:37][CH2:38][CH2:39][CH2:40][CH:35]2[CH3:34])=[O:16])[CH:18]=[C:19]([Cl:21])[CH:20]=1)[C:22]1[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 79742-MethylpiperidineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

Product 1

HCID 53687742HCID 53687742, compoundYield 110.5%

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 (0.060 g) in dichloromethane (4 ml) was added DMF (0.025 ml) followed by 2M oxalyl chloride solution in dichloromethane (0.091 ml). The resultant solution was stirred at room temperature for 1 h, and then 2-methylpiperidine (0.03 g) followed by DIPEA (0.080 ml) were added. After 3 h, the solution was concentrated under reduced pressure and the residue was subjected to preparative hplc. The title compound (0.080 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 solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ac735782b22b4a2392a1f6d08d4cbe5b
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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