Diisopropylethylamine → 3-Chloro-2-(4-((2,4-difluorophenyl)fluoromethyl)piperidin-1-yl)pyrido[3,4-b]pyrazine

HRID 713215Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 4-((2,4-difluorophenyl)fluoromethyl)piperidine hydrochloride (247 mg, 0.929 mmol), 2,3-dichloropyrido[3,4-b]pyrazine (169 mg, 0.845 mmol) and DIPEA (441 μL, 2.53 mmol) in DCM (1.69 mL) was stirred at 0° C. for 5 min then at rt for 30 min. The mixture was then partitioned between EtOAc and saturated aqueous NH4Cl. The organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated. The residue was dissolved in EtOAc and filtered through a pad of silica. The filtrate was concentrated to afford 3-chloro-2-(4-((2,4-difluorophenyl)fluoromethyl)piperidin-1-yl)pyrido[3,4-b]pyrazine (338.4 mg) as a yellow foam. ESI-MS m/z [M+H]+ 393.2.

Workup

waitat rt for 30 min
customThe mixture was then partitioned between EtOAc and saturated aqueous NH4Cl
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
dissolutionThe residue was dissolved in EtOAc
filtrationfiltered through a pad of silica
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-882768c5c74b4169983c6346373d81d8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181249B2

Reaction notes

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