Borane;tetrahydrofuran → HCID 70979752, compound

HRID 1485411Notes

Reaction equation

HRID 1485411 reaction equation
B.C1COCC1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:29](=O)[C:23]3([CH2:25][CH:24]3[C:26]([O-])=[O:27])[C:18]3=[N:19][N:20]=[C:21]([CH3:22])[N:17]3[C:16]3[CH:31]=[CH:32][CH:33]=[CH:34][C:15]2=3)=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:29][C:23]3([CH2:25][CH:24]3[CH2:26][OH:27])[C:18]3=[N:19][N:20]=[C:21]([CH3:22])[N:17]3[C:16]3[CH:31]=[CH:32][CH:33]=[CH:34][C:15]2=3)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 86718498HCID 86718498, compound

Product 1

HCID 70979752HCID 70979752, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BH3-THF complex (1.8 mL, 1M in THF) was added dropwise to a solution of 6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropane]-2′-carboxylate (70 mg, 0.18 mmol) in anhydrous THF (10 mL) at 0° C. The resulting mixture was stirred at room temperature for 48 hrs, then quenched with NH4Cl solution (5 mL), extracted with ethyl acetate (10 mL), dried with Na2SO4, concentrated and purified with prep-HPLC to afford (6-(4-chlorophenyl)-1-methyl-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropan]-2′-yl)methanol (2 mg, 3%) as a white solid.

Workup

  1. customquenched with NH4Cl solution (5 mL)
  2. extractionextracted with ethyl acetate (10 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. custompurified with prep-HPLC

Sources & evidence

ORD record
ord-7584622419c4459db5c184de53224e0b
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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