m-Tolyl isocyanate → HCID 21202035, compound

HRID 1979314Notes

Reaction equation

HRID 1979314 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]=[C:8]=[O:9])[CH:2]=1.[C:11]1([CH3:39])[C:12]([C:17]([CH2:19][N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:23][CH:22]([NH2:37])[C:21]2=[O:38])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1>O1CCCC1>[C:11]1([CH3:39])[C:12]([C:17]([CH2:19][N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:23][CH:22]([NH:37][C:8]([NH:7][C:3]3[CH:4]=[CH:5][CH:6]=[C:1]([CH3:10])[CH:2]=3)=[O:9])[C:21]2=[O:38])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 21201718HCID 21201718, compound

Product 1

HCID 21202035HCID 21202035, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

m-Tolyl isocyanate (34 mg) was added to a solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (90 mg) obtained from Step 2 of Example 18 in tetrahydrofuran (10 ml), the mixture was stirred for 10 minutes at room temperature. The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), to thereby obtain 100 mg of the title compound (Yield: 83%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f730c57778ac485f97d44abd9d60421e
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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