Methanol → HCID 86759099, compound

HRID 394502Notes

Reaction equation

HRID 394502 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=C1)(N1C=CN=C1)=[O:2].[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:16][CH2:15]1.[OH2:27].C[OH:29].[C:30]([O:33][CH2:34][CH3:35])(=[O:32])[CH3:31]>C(Cl)(Cl)Cl.CN(C)C=O>[C:31]([OH:29])(=[O:27])[C:30]([OH:33])=[O:32].[CH2:20]([N:17]1[CH2:18][CH2:19][CH:14]([NH:13][C:1]([NH:8][C:12]2[C:11]3[C:18](=[CH:19][CH:35]=[C:34]([O:33][CH3:30])[N:10]=3)[N:17]=[CH:16][CH:15]=2)=[O:2])[CH2:15][CH2:16]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

8

Reactant 5

HCID 887MethanolHCID 962WaterHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 11788851HCID 11788851, compound

Product 1

HCID 86759099HCID 86759099, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the amine (6d) (0.08, 0.5 mmol) in chloroform (2 ml) was treated with N,N-dimethylaminopyridine (0.06 g, 0.5 mmol) then 1,1′-carbonyldiimidazole (0.11 g, 0.7 mmol). After 2 hours the chloroform was removed by evaporation and the residue treated with a solution of 4-amino-1-heptylpiperidine (0.1 g, 0.5 mmol) in N,N-dimethylformamide (1 ml) and the mixture heated to 100° C. for 1 hour. Water (2 ml) was added dropwise and filtration gave a white solid. Chromatography on silica eluting with a methanol in ethyl acetate gradient afforded the title compound as a white solid, (0.1 g, 50%).

Workup

  1. customAfter 2 hours the chloroform was removed by evaporation
  2. filtrationfiltration
  3. customgave a white solid

Sources & evidence

ORD record
ord-090c00742e7d49d2bdb487cb6aa3bff2
Source dataset
uspto-grants-2003_08
Patent number
US06602882B1

Reaction notes

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