Triethylsilane → 4-(6-Chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone

HRID 2086273Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([N:21]=[C:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17](=[O:34])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17](=[O:34])[CH2:16]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-(6-chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylideneamino]-2-piperazinone (120 mg) in trifluoroacetic acid (1 ml) was combined with triethylsilane (60 mg) and stirred at 50° C. for 4 hours. The reaction mixture was concentrated and the residue was combined with an ice-cooled 1 N aqueous solution of sodium hydroxide, extracted with dichloromethane, dried and then concentrated. The residue obtained was purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1) and crystallized from acetone to obtain the title compound (88 mg) as colorless crystals.

Workup

concentrationThe reaction mixture was concentrated
temperaturecooled 1 N aqueous solution of sodium hydroxide
extractionextracted with dichloromethane
customdried
concentrationconcentrated
customThe residue obtained
customwas purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)
customcrystallized from acetone

Sources & evidence

ORD record: ord-4c92d443e2fd4e679d434cf5158119ab
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723722B1

Reaction notes

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