Borane;tetrahydrofuran → 6-(4-chlorophenyl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine

HRID 1485377Notes

Reaction equation

HRID 1485377 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=O)[CH:13]([CH3:16])[C:12]3=[N:17][N:18]=[C:19]([CH3:20])[N:11]3[C:10]3[CH:21]=[CH:22][CH:23]=[CH:24][C:9]2=3)=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][CH:13]([CH3:16])[C:12]3=[N:17][N:18]=[C:19]([CH3:20])[N:11]3[C:10]3[CH:21]=[CH:22][CH:23]=[CH:24][C:9]2=3)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 709790516-(4-chlorophenyl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one

Product 1

HCID 709792556-(4-chlorophenyl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepineYield 7.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-chlorophenyl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one (40.0 mg, 0.12 mmol) in THF (5 ml) was added BH3-THF solution (1 mL, 1M in THF) slowly, the resulting mixture was stirred under reflux overnight, concentrated, the residue was purified by Prep-HPLC (column: Gemini 5u C18 250*21.5 mm; mobile: H2O (0.1% TFA)-ACN(0.1% TFA)) to give 6-(4-chlorophenyl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine as an off-white solid (3.0 mg, 7.8%).

Workup

  1. temperatureunder reflux overnight
  2. concentrationconcentrated
  3. customthe residue was purified by Prep-HPLC (column: Gemini 5u C18 250*21.5 mm; mobile: H2O (0.1% TFA)-ACN(0.1% TFA))

Sources & evidence

ORD record
ord-d55b474877f6409c861a7c373df06c21
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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