Acetic Acid → HCID 22005532, compound

HRID 324784

Reaction equation

HRID 324784 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][C:28]=1[N+:35]([O-:37])=[O:36].Cl.[C:39]([C:42]1[O:43][CH:44]=[CH:45][CH:46]=1)(=[NH:41])[NH2:40].N1CCOCC1.C(O)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)C>[O:43]1[CH:44]=[CH:45][CH:46]=[C:42]1[C:39]1[NH:41][C:11]([CH2:10][O:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:14])[CH:31]([C:30]2[CH:33]=[CH:34][C:27]([CH3:26])=[C:28]([N+:35]([O-:37])=[O:36])[CH:29]=2)[N:40]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8083MorpholineHCID 24436Sodium SulfateHCID 17989983-Nitro-p-tolualdehydeHCID 12231049Furan-2-carboximidamide hydrochlorideHCID 220055123-Phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate

Product 1

HCID 22005532HCID 22005532, compoundYield 0.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate (10.0 g, 28.78 mmol), 4-methyl-3-nitrobenzaldehyde (4.75 g, 28.78 mmol), 2-amidinofuran hydrochloride (4.20 g, 28.78 mmol), morpholine (3.75 ml, 43.17 mmol), acetic acid (3.29 ml, 57.56 mmol), and sodium sulfate (8.17 g, 57.56 mmol) was stirred in ethanol (50 ml) for 1 hour at room temperature and then heated to 50° C. for 7 days. The ethanol was removed in vacuo and ethyl acetate was added to the residue. The mixture was filtered 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 and RP-HPLC (twice) to give the title compound (150 mg) as an oil. Electrospray MS m/z 587 [M+H]+.

Workup

  1. customThe ethanol was removed in vacuo and ethyl acetate
  2. additionwas added to the residue
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed with water, sodium hydrogen carbonate solution and brine
  5. customdried
  6. customevaporated
  7. customto yield an oil
  8. customThe oil was further purified by flash chromatography and RP-HPLC (twice)

Sources & evidence

ORD record
ord-25ce43649d774d819074daa971a8dfd7
Source dataset
uspto-grants-2001_04
Patent number
US06218538B1

Linked notes

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