Triethylamine → N-[(5-methyl-1-triphenylmethyl-1H-imidazol-4-yl)methyl]-5,6-dihydro-4H-pyrrolo [3,2,1-ij]quinoline-1-carboxamide

HRID 1029513Notes

Reaction equation

HRID 1029513 reaction equation
[C:1]1([C:13]([OH:15])=O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.S(Cl)(Cl)=O.[CH3:20][C:21]1[N:25]([C:26]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[N:23][C:22]=1[CH2:45][NH:46]C.C(N(CC)CC)C>C(#N)C>[CH3:20][C:21]1[N:25]([C:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:24]=[N:23][C:22]=1[CH2:45][NH:46][C:13]([C:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1)=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 153083055-methyl-4-(methylamino)methyl-1-triphenylmethyl-1H-imidazoleHCID 225568865,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid

Product 1

HCID 54177960N-[(5-methyl-1-triphenylmethyl-1H-imidazol-4-yl)methyl]-5,6-dihydro-4H-pyrrolo [3,2,1-ij]quinoline-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.2 g (6.0 mmol) of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid were mixed with 15 ml of thionyl chloride and boiled for 2.5 hours. The excess of thionyl chloride was distilled off in vacuo, and toluene was added. The mixture was evaporated in vacuo again, and the residue was dissolved in 20 ml of acetonitrile. A solution of 2.2 g (6.0 mmol) of 5-methyl-4-(methylamino)methyl-1-triphenylmethyl-1H-imidazole and 1.7 ml (12 mmol) of triethyl amine in 25 ml of acetonitrile was added, the mixture was boiled for 1 hour, and evaporated in vacuo. The residue was shaken with methylene chloride and 2 N NaOH. The organic layer was washed with water and evaporated in vacuo. The residue was chromatographed on silicagel using methylene chloride/methanol (95/5) as an eluent. After evaporating the desired fractions 2.0 g of N-methyl, N-[(5-methyl-1-triphenylmethyl-1H-imidazol-4-yl)methyl]-5,6-dihydro-4H-pyrrolo [3,2,1-ij]quinoline-1-carboxamide were obtained. This product was treated as described in Example I to remove the triphenylmethyl group, and purified. 0.46 g of the desired title compound were obtained.

Workup

  1. distillationThe excess of thionyl chloride was distilled off in vacuo, and toluene
  2. additionwas added
  3. customThe mixture was evaporated in vacuo again
  4. dissolutionthe residue was dissolved in 20 ml of acetonitrile
  5. waitthe mixture was boiled for 1 hour
  6. customevaporated in vacuo
  7. washThe organic layer was washed with water
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on silicagel
  10. customAfter evaporating the desired fractions 2.0 g of N-methyl

Sources & evidence

ORD record
ord-4edf9aeefe7142d5aec2641b7f5f2c98
Source dataset
uspto-grants-1992_04
Patent number
US05102901

Reaction notes

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