4-Amino-2,2,6,6-tetramethylpiperidine → 7-(1-tert-butylpiperidin-4-yl)-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

HRID 394146Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:20])[N:9]2[C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[N:3]=1.N[CH:29]1[CH2:34][C:33](C)(C)[NH:32][C:31](C)(C)[CH2:30]1>CS(C)=O>[C:5]([N:32]1[CH2:31][CH2:30][CH:29]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8](=[O:20])[N:9]3[C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])=[C:4]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[N:3]=2)[CH2:34][CH2:33]1)([CH3:10])([CH3:6])[CH3:4]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 200 mg of 7-bromo-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (COMPOUND HHH2) and 1 mL of 4-amino-2,2,6,6-tetramethylpiperidine in 0.5 mL of DMSO was stirred at 130° C. for 3 h. The mixture was cooled, filtered, and purified by reverse-phase preparative HPLC (YMC C18 100×50 mm column; 10:90 to 90:10 v/v acetonitrile/water+0.1% TFA over 15 min; 20 mL/min) to yield the title compound. Mass spectrum (ESI) 557 (M+1). 1H NMR (500 MHz, CD3OD): selected peaks δ 1.32-1.58 (m, 14H), 2.05-2.24 (m, 2H), 4.40 (br s, 1H).

Workup

temperatureThe mixture was cooled
filtrationfiltered
custompurified by reverse-phase preparative HPLC (YMC C18 100×50 mm column; 10:90 to 90:10 v/v acetonitrile/water+0.1% TFA over 15 min; 20 mL/min)

Sources & evidence

ORD record: ord-53bde892f64d4515a1d8b5e197e0dfe1
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

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