Ammonium Chloride → 2-(6-(4-chlorophenyl)-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl) ethanol

HRID 1485403Notes

Reaction equation

HRID 1485403 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=O)[CH:13]([CH2:16][C:17](O)=[O:18])[C:12]3=[N:20][N:21]=[C:22]([CH3:23])[N:11]3[C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)=[CH:4][CH:3]=1.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH:13]([CH2:16][CH2:17][OH:18])[C:12]3=[N:20][N:21]=[C:22]([CH3:23])[N:11]3[C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 709789952-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetic acid

Product 1

HCID 709790752-(6-(4-chlorophenyl)-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl) ethanolYield 19.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetic acid (500 mg, 1.32 mmol) in THF (300 ml) was added BH3 solution in THF (1 M, 6.5 mL) dropwise, the resulting mixture was stirred at room temperature overnight. NH4Cl aqueous (15 mL) was added, and then extracted with DCM (3×30 mL), the combined organic layers were dried over Na2SO4, and the solvent was removed in vacuum. The residue was purified by flash chromatography eluting with DCM:MeOH=40:1 to give 2-(6-(4-chlorophenyl)-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)ethanol as an off-white solid (90 mg, 18.5%).

Workup

  1. extractionextracted with DCM (3×30 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. customthe solvent was removed in vacuum
  4. customThe residue was purified by flash chromatography
  5. washeluting with DCM

Sources & evidence

ORD record
ord-b2624bbf5f9a4dde9db3f65370837b52
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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