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Triethylamine → 1-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-methylphenyl)urea

HRID 1979392
Notes
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Reaction equation

HRID 1979392 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:32]1([CH3:61])[C:33]([C:38]([CH2:40][N:41]2[C:47]3[CH:48]=[C:49]([CH3:52])[CH:50]=[CH:51][C:46]=3[N:45]([C:53](=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:44][CH:43]([NH2:59])[C:42]2=[O:60])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1>O1CCCC1>[C:32]1([CH3:61])[C:33]([C:38]([CH2:40][N:41]2[C:47]3[CH:48]=[C:49]([CH3:52])[CH:50]=[CH:51][C:46]=3[N:45]([C:53](=[O:58])[C:54]([CH3:55])([CH3:56])[CH3:57])[CH2:44][CH:43]([NH:59][C:14]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=3)=[O:16])[C:42]2=[O:60])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 15049977Methyl 5-Amino-2-methylbenzoateHCID 212016171-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212019191-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-methylphenyl)urea
Yield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 5-amino-2-methylbenzoate (223 mg) was dissolved in tetrahydrofuran (30 ml), under ice-cooling triphosgene (135 mg) was added, triethylamine (116 μl) was added thereto five times every 3 minutes, the mixture was stirred for 10 minutes at same temperature. Subsequently, a solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (500 mg) in tetrahydrofuran (20 ml) was added dropwise, stirred for 30 minutes at same temperature, and then stirred for 3 hours at room temperature. The reaction mixture was concentrated under reduced pressure, water (50 ml) was added, and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography(chloroform:ethyl acetate=10:1), to thereby obtain 271 mg of the titled compound.

Workup

  1. additionwas added
  2. stirringstirred for 30 minutes at same temperature
  3. stirringstirred for 3 hours at room temperature
  4. concentrationThe reaction mixture was concentrated under reduced pressure, water (50 ml)
  5. additionwas added
  6. extractionextracted with methylene chloride
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography(chloroform:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-6cacce849d184845b5fe4906145a0729
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06239131B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes