Diisopropylethylamine → (5-Chloro-2-fluorophenyl)(1-(3-chloropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)methanone

HRID 713227Notes

Reaction equation

HRID 713227 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([F:17])=[C:7]([C:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:10])[CH:8]=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:2][C:3]1[CH:4]=[CH:5][C:6]([F:17])=[C:7]([C:9]([CH:11]2[CH2:12][CH2:13][N:14]([C:19]3[N:20]=[C:21]4[CH:29]=[CH:28][N:27]=[CH:26][C:22]4=[N:23][C:24]=3[Cl:25])[CH2:15][CH2:16]2)=[O:10])[CH:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 231227312,3-Dichloropyrido[3,4-b]pyrazineHCID 49761186(5-Chloro-2-fluorophenyl)(piperidin-4-YL)methanone hydrochloride

Product 1

HCID 118159129(5-Chloro-2-fluorophenyl)(1-(3-chloropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)methanoneYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (5-chloro-2-fluorophenyl)(piperidin-4-yl)methanone hydrochloride (153 mg, 0.550 mmol), 2,3-dichloropyrido[3,4-b]pyrazine (100 mg, 0.500 mmol) and DIPEA (261 μL, 1.500 mmol) in DCM (1.67 mL) was stirred at rt for 30 min. The mixture was partitioned between aqueous NH4Cl and EtOAc. The organic layer was filtered through a pad of silica, washing with EtOAc, and the filtrate was concentrated under reduced pressure to give (5-chloro-2-fluorophenyl)(1-(3-chloropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)methanone (205.5 mg) as an orange solid. ESI-MS m/z [M+H]+ 405.2.

Workup

  1. customThe mixture was partitioned between aqueous NH4Cl and EtOAc
  2. filtrationThe organic layer was filtered through a pad of silica
  3. washwashing with EtOAc
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6a64a1834d694db8ba1b23f654bb6b55
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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