Triethylamine → HCID 54511962, compound

HRID 1979342Notes

Reaction equation

HRID 1979342 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:7][C:6](=[N:22][OH:23])[C:5]1=[O:24].[CH2:25]([N:28]=[C:29]=[O:30])[CH2:26][CH3:27].C(N(CC)CC)C>O1CCCC1>[CH3:1][O:2][CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:7][C:6](=[N:22][O:23][C:29]([NH:28][CH2:25][CH2:26][CH3:27])=[O:30])[C:5]1=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 86756977HCID 86756977, compound

Product 1

HCID 54511962HCID 54511962, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methoxymethyl-2-oxo-3-hydroxyimino-5-(2-fluorophenyl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (2.35 g) was dissolved in tetrahydrofuran (25 ml), propyl isocyanate (1.52 g) and triethylamine (1.81 g) were added thereto, and the mixture was refluxed for 3 hours. The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (silica gel NH-DM1020, produced by Fujisilicia Co. Ltd., chloroform), to thereby obtain 2.52 g of the titled compound as brown amorphous (Yield: 85%).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (silica gel NH-DM1020, produced by Fujisilicia Co. Ltd., chloroform)

Sources & evidence

ORD record
ord-4a12faefb7c44709a19e47747fb05ef5
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

Loading…