m-Tolyl isocyanate → 1-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methylphenyl)urea

HRID 1979297Notes

Reaction equation

HRID 1979297 reaction equation
[C:1]1([CH3:29])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:13][CH:12]([NH2:27])[C:11]2=[O:28])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:30]1([CH3:39])[CH:35]=[CH:34][CH:33]=[C:32]([N:36]=[C:37]=[O:38])[CH:31]=1>O1CCCC1>[C:1]1([CH3:29])[C:2]([C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([C:21](=[O:26])[C:22]([CH3:24])([CH3:25])[CH3:23])[CH2:13][CH:12]([NH:27][C:37]([NH:36][C:32]3[CH:33]=[CH:34][CH:35]=[C:30]([CH3:39])[CH:31]=3)=[O:38])[C:11]2=[O:28])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 212016481-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212018471-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methylphenyl)ureaYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (411 mg) was dissolved in tetrahydrofuran. m-Tolyl isocyanate (146 mg) was added thereto, and the resultant mixture was stirred at room temperature for 30 minutes. The solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), to thereby obtain 300 mg of the title compound.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5d19ed7ef68f4cbbba32ba8d65fa6973
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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