Sodium Iodide → 6-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-pyrido[3,4-b]pyrazine

HRID 1713141Notes

Reaction equation

HRID 1713141 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[CH2:7][NH:8][CH2:9][CH2:10][C:2]=12.[Na+].[I-].C([O-])([O-])=O.[K+].[K+].Cl[CH2:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH:29]2[CH2:32][CH2:31][CH2:30]2)[CH2:25][CH2:24]1)=[O:22]>C(#N)C.C(Cl)Cl>[CH:29]1([N:26]2[CH2:27][CH2:28][N:23]([C:21](=[O:22])[CH2:20][N:8]3[CH2:9][CH2:10][C:2]4[C:3](=[N:4][CH:5]=[CH:6][N:1]=4)[CH2:7]3)[CH2:24][CH2:25]2)[CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 552655945H,6H,7H,8H-pyrido[3,4-b]pyrazineHCID 574205621-(Chloroacetyl)-4-cyclobutylpiperazine

Product 1

HCID 574207226-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-pyrido[3,4-b]pyrazine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine (70 mg, 0.518 mmol), NaI (50 mg, 0.333 mmol), and K2CO3 (200 mg, 1.45 mmol) in acetonitrile is added 2-chloro-1-(4-cyclobutyl-piperazin-1-yl)-ethanone (112 mg, 0.518 mmol). The mixture is stirred overnight at rt, diluted with DCM (20 mL) and filtered through Celite. The filtrate is evaporated and the crude product is purified by silica gel chromatography eluting with EtOAc/MeOH/NEt3 (95:5:5) to yield the title compound. 1H NMR (300 MHz, CDCl3) δ 8.35 (2H, dd), 3.85 (2H, s), 3.70-3.66 (m, 4H), 3.46 (2H, s), 3.09 (2H, t), 2.96 (2H, t), 2.75 (1H, m), 2.37-2.34 (4H, m), 2.09-1.67 (m, 6H); MS (+VE) m/z 316.21 (M++1).

Workup

  1. filtrationfiltered through Celite
  2. customThe filtrate is evaporated
  3. customthe crude product is purified by silica gel chromatography
  4. washeluting with EtOAc/MeOH/NEt3 (95:5:5)

Sources & evidence

ORD record
ord-f8e9205dc2ce46b09e081bf008ee17d4
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

Loading…