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

HRID 713205Notes

Reaction equation

HRID 713205 reaction equation
Cl.[F:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]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:9]1[CH2:8][CH2:7][CH:6]([O:5][C:4]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:3]=2[F:2])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 231227312,3-Dichloropyrido[3,4-b]pyrazineHCID 1181591584-(2-Fluoro-4-methoxyphenoxy)piperidine hydrochloride

Product 1

HCID 1181593503-Chloro-2-(4-(2-fluoro-4-methoxyphenoxy)piperidin-1-yl)pyrido[3,4-b]pyrazineYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-fluoro-4-methoxyphenoxy)piperidine hydrochloride (144 mg, 0.550 mmol), 2,3-dichloropyrido[3,4-b]pyrazine (100 mg, 0.500 mmol) and DIPEA (260 μL, 1.500 mmol) in DCM (1.0 mL) was stirred at room temperature 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 silica pad. The filtrate was concentrated to afford the crude title compound (200.7 mg, 100%) as a yellow oil, which was used without further purification. ESI-MS m/z [M+F]+ 389.2.

Workup

  1. customThe mixture was then partitioned between EtOAc and saturated aqueous NH4Cl
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was dissolved in EtOAc
  7. filtrationfiltered through a silica pad
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-424d69d6fd9d4cceb76a6b9704798b3f
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

Loading…