Water → HCID 18917572, compound

HRID 234065Notes

Reaction equation

HRID 234065 reaction equation
[NH2:1][C:2]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[N:4]2[C:20]([CH3:23])=[N:21][N:22]=[C:3]12.[CH3:29][C:30]1[CH:31]=[C:32]([N:36]=[C:37]=[O:38])[CH:33]=[CH:34][CH:35]=1.O>O1CCCC1>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[C:6]3[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=3[N:4]3[C:20]([CH3:23])=[N:21][N:22]=[C:3]3[C:2]([NH:1][C:37]([NH:36][C:32]3[CH:33]=[CH:34][CH:35]=[C:30]([CH3:29])[CH:31]=3)=[O:38])([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:8]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 69303m-Tolyl isocyanateHCID 18917584HCID 18917584, compound

Product 1

HCID 18917572HCID 18917572, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a nitrogen atmosphere, 4-amino-6-(4-chlorophenyl)-4-ethoxycarbonyl-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]-benzodiazepine (373 mg) was dissolved in dry tetrahydrofuran (4 ml) and thereto was added 3-methylphenyl isocyanate (139 μl), followed by reaction at room temperature for 3.5 hours. After the completion of the reaction, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a 5% aqueous solution of citric acid, water and saturated brine, and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (chroloform:methanol=45:1) and crystallized to give 219 mg of N-[6-(4-chlorophenyl)-4-ethoxycarbonyl-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]-N'-(3-methylphenyl)urea as pale yellow needle crystals, mp. 168°-172° C.

Workup

  1. customfollowed by reaction at room temperature for 3.5 hours
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a 5% aqueous solution of citric acid, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe residue was concentrated under reduced pressure
  7. customThe concentrate was purified by silica gel column chromatography (chroloform:methanol=45:1)
  8. customcrystallized

Sources & evidence

ORD record
ord-65d052431f28499c8e38c768c5a0e678
Source dataset
uspto-grants-1997_01
Patent number
US05593988

Reaction notes

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