Boron Trichloride → HCID 69211615, compound

HRID 30062Notes

Reaction equation

C([O:8][CH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C:13]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)[CH2:25][CH2:24]2)=[N:12][N:11]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCl>[OH:8][CH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C:13]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)[CH2:25][CH2:24]2)=[N:12][N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 120 mg of 4-benzyloxymethyl-7-methoxy-N-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]phthalazin-1-amine in 4 mL of dichloromethane is stirred under nitrogen at 0° C., followed by dropwise addition of 2.3 mL of a molar solution of boron trichloride in dichloromethane. The reaction medium is stirred for 1 hour at 0° C. and then for 30 minutes at room temperature. It is hydrolysed with aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic phase is washed with water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue is purified on a column of silica (eluent: 100/0 to 85/15 v/v dichloromethane/methanol). 58 mg of product are obtained in the form of a beige-coloured powder.

Workup

waitfor 30 minutes at room temperature
extractionextracted with dichloromethane
washThe organic phase is washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe residue is purified on a column of silica (eluent: 100/0 to 85/15 v/v dichloromethane/methanol)

Sources & evidence

ORD record: ord-191cd4dbd06c46a684baff88706f32a3
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423030B2

Reaction notes

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