Diisopropylethylamine → (S)-3-(3-chloro-5-(trifluoromethyl)pyridin-2-ylamino)-1'-(5-chloropyrazin-2-yl)-[1,4'-bipiperidin]-2-one

HRID 407971Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A flask was charged with (S)-3-(3-chloro-5-(trifluoromethyl)pyridin-2-ylamino)-1,4′-bipiperidin-2-one hydrochloride (0.075 g, 0.18 mmol), 2,5-dichloropyrazine (0.030 g, 0.20 mmol), Hunig's base (0.095 mL, 0.54 mmol), and DMF (3 mL). The reaction was stirred at 100° C. overnight. The organic solvents were removed under reduced pressure. The residue was purified using silica gel column chromatography with 50-100% ethyl acetate in hexanes to provide (S)-3-(3-chloro-5-(trifluoromethyl)pyridin-2-ylamino)-1′-(5-chloropyrazin-2-yl)-[1,4′-bipiperidin]-2-one (0.037 g, 0.076 mmol, 42% yield) as yellow solid. Mass spectrum (apci) m/z=489.2 (M+H).

Workup

customThe organic solvents were removed under reduced pressure
customThe residue was purified

Sources & evidence

ORD record: ord-5f12a1f812d6485ab572c4b08c4deead
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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