Triethylamine → 3-Chloro-2-(4-(2,4-difluorobenzyl)piperazin-1-yl)pyrido[3,4-b]pyrazine

HRID 713204Notes

Reaction equation

HRID 713204 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]2=[N:6][C:7]=1[Cl:8].[F:13][C:14]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:15]=1[CH2:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)CC)C>C(Cl)Cl>[Cl:8][C:7]1[N:6]=[C:5]2[CH:9]=[N:10][CH:11]=[CH:12][C:4]2=[N:3][C:2]=1[N:20]1[CH2:19][CH2:18][N:17]([CH2:16][C:15]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:14]=2[F:13])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27828061-(2,4-Difluorobenzyl)piperazineHCID 231227312,3-Dichloropyrido[3,4-b]pyrazine

Product 1

HCID 1181593003-Chloro-2-(4-(2,4-difluorobenzyl)piperazin-1-yl)pyrido[3,4-b]pyrazineYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2,3-dichloropyrido[3,4-b]pyrazine (8 g, 40.0 mmol) and 1-(2,4-difluorobenzyl)piperazine (8.49 g, 40.0 mmol) in DCM (100 mL) was added triethylamine (16.72 mL, 120 mmol) at room temperature. Then the mixture was stirred at room temperature for 0.5 h. The reaction mixture was diluted with 30 mL of DCM, washed with brine twice, dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel chromatography, eluting with a gradient of 50:1 to 5:1 PE:EtOAc to give the title compound (12 g, 80%). ESI-MS m/z [M+H]+ 376.0.

Workup

  1. washwashed with brine twice
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with a gradient of 50:1 to 5:1 PE

Sources & evidence

ORD record
ord-22913d9167484588bf7c9044f8842326
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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