Piperidine → HCID 50882150, compound

HRID 2075586Notes

Reaction equation

HRID 2075586 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:37](N2CCCCC2)=[O:38])[C:8]([O:35][CH3:36])=[C:9]([NH:11]C(=O)C(C2C3C(=CC=CC=3)C(OCCN3CCOCC3)=CC=2)=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=[O:47].CCN(C(C)C)C(C)C.N1CCCCC1>C(Cl)Cl.CN(C=O)C>[NH2:11][C:9]1[C:8]([O:35][CH3:36])=[C:7]([CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:10]=1)[C:37]([OH:38])=[O:47]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 11342430HCID 11342430, compound

Product 1

HCID 50882150HCID 50882150, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-[5-tert-Butyl-2-methoxy-3-(piperidine-1-carbonyl)-phenyl]-2-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-2-oxo-acetamide (31) 26 mg (0.049 mmol) of the compound obtained above was converted to the acid chloride by reaction with oxalyl chloride (54 μl, 0.5 mmol) in 0.5 mL DCM in the presence of a catalytic amount of DMF (rt, 2 h). After removal of the solvent, the crude acid chloride was dissolved in 1 mL DCM. DIEA (0.2 mmol) was added, followed by the addition of piperidine (0.1 mmol). The resulting mixture was stirred at rt overnight. Aqueous work-up and purification by LC-MS resulted in 7.6 mg pure product. Calculated mass=602. Observed mass=602

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe crude acid chloride was dissolved in 1 mL DCM
  3. customAqueous work-up and purification by LC-MS

Sources & evidence

ORD record
ord-8c347d71895a4997a398798dae00d64c
Source dataset
uspto-grants-2011_04
Patent number
US07919617B2

Reaction notes

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