Piperidine → 3-Phenylpropyl 4-(3,4-dichlorophenyl)-2-(2-furyl)-6-[(2-(4-methyl-1-piperazinyl)ethoxy)methyl]-1,4-dihydropyrimidine-5-carboxylate

HRID 324780Notes

Reaction equation

HRID 324780 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:15])[CH2:4][CH2:3]1.[Cl:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH:31]=O.Cl.[C:38]([C:41]1[O:42][CH:43]=[CH:44][CH:45]=1)(=[NH:40])[NH2:39].N1CCCCC1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(O)(=O)C>[Cl:27][C:28]1[CH:29]=[C:30]([CH:31]2[C:13]([C:14]([O:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])=[C:12]([CH2:11][O:10][CH2:9][CH2:8][N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[NH:40][C:38]([C:41]3[O:42][CH:43]=[CH:44][CH:45]=3)=[N:39]2)[CH:33]=[CH:34][C:35]=1[Cl:36]

Participants

8

Reactant 5

HCID 8082PiperidineHCID 227103,4-DichlorobenzaldehydeHCID 516892Sodium BicarbonateHCID 12231049Furan-2-carboximidamide hydrochlorideHCID 220055573-Phenylpropyl 4-(2-(4-methyl-1-piperazinyl)ethoxy)acetoacetate

Product 1

HCID 49132183-Phenylpropyl 4-(3,4-dichlorophenyl)-2-(2-furyl)-6-[(2-(4-methyl-1-piperazinyl)ethoxy)methyl]-1,4-dihydropyrimidine-5-carboxylateYield 5.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-phenylpropyl 4-(2-(4-methyl-1-piperazinyl)ethoxy)acetoacetate (500 mg, 1.38 mmol), 3,4-dichlorobenzaldehyde (241.5 mg, 1.38 mmol), 2-amidinofuran hydrochloride (202.3 mg, 1.38 mmol) and catalytic amounts of piperidine (1 μL) and acetic acid (10 μL) was stirred in N,N-dimethylformamide (5 mL) for 2 days at room temperature. Sodium hydrogen carbonate was added and the reaction mixture was stirred for an additional 5 days at room temperature before heating to 60° C. for 3 days. The DMF was removed in vacuo and ethyl acetate was added to the residue. The precipitate was removed by filtration and the filtrate was washed with water, sodium hydrogen carbonate solution and brine, dried and evaporated to yield an oil. The oil was further purified by flash chromatography to give the title compound (48 mg) as an oil. Electrospray MSm/z 611/613 [M+H]+.

Workup

  1. temperaturebefore heating to 60° C. for 3 days
  2. customThe DMF was removed in vacuo and ethyl acetate
  3. additionwas added to the residue
  4. customThe precipitate was removed by filtration
  5. washthe filtrate was washed with water, sodium hydrogen carbonate solution and brine
  6. customdried
  7. customevaporated
  8. customto yield an oil
  9. customThe oil was further purified by flash chromatography

Sources & evidence

ORD record
ord-63363d53855f487da49e828a41b7e25f
Source dataset
uspto-grants-2001_04
Patent number
US06218538B1

Reaction notes

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