Potassium Carbonate → methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-4-amino-1H-imidazole-5-carboxylate

HRID 1650999Notes

Reaction equation

HRID 1650999 reaction equation
[CH2:1]1[CH:14]2[CH:5]([CH2:6][C:7]3[C:12]([CH:13]2[NH:15][CH:16]=[N:17][C:18]#[N:19])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1.[C:20](=O)([O-])[O-].[K+].[K+].Br[CH:27](C)[C:28]([O-:30])=[O:29]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[CH2:1]1[CH:14]2[CH:5]([CH2:6][C:7]3[C:12]([CH:13]2[N:15]2[C:27]([C:28]([O:30][CH3:20])=[O:29])=[C:18]([NH2:19])[N:17]=[CH:16]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 14535398Alpha-bromopropionateHCID 178512230HCID 178512230, compound

Product 1

HCID 23050704methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-4-amino-1H-imidazole-5-carboxylateYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 2855718-Crown-6Solvent

Procedure

20.8 Parts of N-(1,2,3,4,4a,9,9a,10-octahydroanthracene-9-yl)-N'-cyano-formamidine were dissolved in 140 ml of N,N-dimethylformamide together with 0.1 parts of 18-crown-6. 28.4 Parts of potassium carbonate were added. The mixture was heated to +80° C. and 13.8 Parts of α-bromo-methyl-acetate were added. After 15 hours at +80° C. to +100° C. the reactants were poured on ice and the mixture was extracted with ether. The etheral extracts were dried with Na2SO4, filtered and concentrated. 21 Parts of crude residue were chromatographed on a silica gel column and extracted with an ethyl acetate/hexane mixture (1:1). 11.6 Parts (43%) of methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracene-9-yl)-4amino-1H-imidazole-5-carboxylate (int. 15), mp. 155-159° C. were isolated.

Workup

  1. temperatureThe mixture was heated to +80° C.
  2. additionAfter 15 hours at +80° C. to +100° C. the reactants were poured on ice
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe etheral extracts were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custom21 Parts of crude residue were chromatographed on a silica gel column
  8. extractionextracted with an ethyl acetate/hexane mixture (1:1)

Sources & evidence

ORD record
ord-8602da9df2cb4871b69c1d96b50b5e72
Source dataset
uspto-grants-1990_05
Patent number
US04927449

Reaction notes

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