Triethylamine → HCID 19592866, compound

HRID 613557Notes

Reaction equation

HRID 613557 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH2:17][OH:18])=[C:12]2[N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)=[O:5].C(N([CH2:34][CH3:35])CC)C.Cl[C:37]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:38]>ClCCl>[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:3]=1[C:4]([N:6]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH2:17][O:18][C:37]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:38])=[C:12]2[N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[C:37]([O:39][C:35]1[CH:34]=[CH:42][CH:41]=[CH:40][CH:45]=1)=[O:38])[C:37]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:38])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformate2×HCID 19592507HCID 19592507, compound

Product 1

HCID 19592866HCID 19592866, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 8-(2,6-dichlorobenzoylamino)-3-hydroxymethyl-4-(imidazol-1-yl)quinoline (300 mg) in dichloromethane (5 ml) were dropwise added triethylamine (294 mg) and phenyl chloroformate (375 mg) under ice-cooling, and the mixture was stirred for 2.5 hours at ambient temperature. To the mixture was further added phenyl chloroformate (250 mg), and the mixture was stirred for 1.5 hours at ambient temperature. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane, and phenyl chloroformate (375 mg) and diisopropylethylamine (0.506 ml) were added thereto. The mixture was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel (ethyl acetate-n-hexane) to give 8-[N-(2,6-dichlorobenzoyl)-N-phenoxycarbonylamino]-4-[2-(phenoxycarbonyl)imidazol-1-yl]-3-(phenoxycarbonyloxymethyl)quinoline (250 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1.5 hours at ambient temperature
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. additionphenyl chloroformate (375 mg) and diisopropylethylamine (0.506 ml) were added
  7. customThe mixture was evaporated in vacuo
  8. customthe residue was purified by flash chromatography on silica gel (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-0db28fed14c14fcda0fd8614e940687d
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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