Phenyl isocyanate → 1-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-phenylurea

HRID 1979469Notes

Reaction equation

HRID 1979469 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([C:14]([CH2:16][N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:20][CH:19]([NH2:34])[C:18]1=[O:35])=[O:15])([CH3:13])([CH3:12])[CH3:11]>O1CCCC1>[C:10]([C:14]([CH2:16][N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:20][CH:19]([NH:34][C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:9])[C:18]1=[O:35])=[O:15])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 154908351-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212015561-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-phenylureaYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl isocyanate (110 mg) was added to a solution of 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (300 mg) in anhydrous tetrahydrofuran (10 ml), the mixture was stirred for 10 minutes at room temperature. The reaction mixture was concentrated under reduced pressure, etanol was added to the residue for crystallization, collected by filtration, to thereby obtain 336 mg of the title compound (Yield 83.9%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, etanol
  2. additionwas added to the residue for crystallization
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-18dd72bdc1914fd8a73714011bb28c5e
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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