Boron Trichloride → HCID 136088557, compound

HRID 1051076Notes

Reaction equation

HRID 1051076 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH:5]1[C:13]2[C:8](=[C:9]([C:14]3[N:18]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]([O:27]C(C)C)=[C:23]([CH:26]=4)[C:24]#[N:25])[O:16][N:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1.B(Cl)(Cl)Cl>ClCCCl>[OH:27][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[O:16][N:15]=[C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:8]=3[CH2:7][CH2:6][CH:5]4[NH:4][CH2:3][CH2:2][OH:1])[N:18]=2)=[CH:26][C:23]=1[C:24]#[N:25]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 25110515HCID 25110515, compound

Product 1

HCID 136088557HCID 136088557, compoundYield 671.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To 5-(3-(1-((2-hydroxyethyl)amino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile (15.0 mg, 0.37 mmol) in DCE (3 mL) was added BCl3 (1.85 mL of 1M DCM solution). The reaction mixture was stirred at room temperature for 18 hrs. The solvent was evaporated, and the residue purified by chromatography (DCM/MeOH) to give 900.0 mg (67%) of 2-hydroxy-5-(3-(1-((2-hydroxyethyl)amino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)benzonitrile 102 as white solid. LCMS-ESI (m/z) calculated for C20H18N4O3: 362.4. found 363.1 [M+H]+, tR=2.13 min. Enantiomerically pure materials can be obtained in an analogous fashion from (R)- or (S)-5-(3-(1-(2-hydroxyethylamino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-d161057bf25144ecbe76ee94bc24ad7a
Source dataset
uspto-grants-2016_07
Patent number
US09388147B2

Reaction notes

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