6-(4-chlorophenyl)-4-ethyl-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one → 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one

HRID 1485426Notes

Reaction equation

HRID 1485426 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH:13](CC)[C:12]3=[N:18][N:19]=[C:20]([CH3:21])[N:11]3[C:10]3[CH:22]=[CH:23][CH:24]=[CH:25][C:9]2=3)=[CH:4][CH:3]=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12]3=[N:18][N:19]=[C:20]([CH3:21])[N:11]3[C:10]3[CH:22]=[CH:23][CH:24]=[CH:25][C:9]2=3)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 709792176-(4-chlorophenyl)-4-ethyl-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one

Product 1

HCID 709795286-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-oneYield 13.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 50 mL flask evacuated and brimmed with dry nitrogen, was charged with a solution of 6-(4-chlorophenyl)-4-ethyl-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one (10.0 mg, 0.028 mmol) in tetrahydrofuran (5 mL). To this mixture was added borane-tetrahydrofuran complex solution (1 mol/L, 1 mL) slowly. The mixture was stirred for 12 hours at reflux, quenched by hydrochloric acid aqueous (1.0 mol/L, 1 mL) to adjust pH>7 and extracted with ethyl acetate (5 mL*3). The organic layer was concentrated to give a residue. The residue was purified by prep-HPLC (Phenomenex C18 (150 mm*21.2 mm*5 um), acetonitrile/water=1:100 (0.1% formic acid), flow rate: 30 mL/min) to give 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one as an off-white solid (1.2 mg, 12%).

Workup

  1. customInto a 50 mL flask evacuated
  2. temperatureat reflux
  3. customquenched by hydrochloric acid aqueous (1.0 mol/L, 1 mL)
  4. extractionextracted with ethyl acetate (5 mL*3)
  5. concentrationThe organic layer was concentrated
  6. customto give a residue
  7. customThe residue was purified by prep-HPLC (Phenomenex C18 (150 mm*21.2 mm*5 um), acetonitrile/water=1:100 (0.1% formic acid), flow rate: 30 mL/min)

Sources & evidence

ORD record
ord-5357896ac87f46de8d2d33eb18bd11f6
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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