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

HRID 1713143Notes

Reaction equation

HRID 1713143 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]3[CH2:16][CH2:15][NH:14][CH2:13][C:10]3=[N:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+].Cl[CH2:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([CH:35]2[CH2:38][CH2:37][CH2:36]2)[CH2:31][CH2:30]1)=[O:28]>C(#N)C.C(Cl)Cl>[CH:35]1([N:32]2[CH2:33][CH2:34][N:29]([C:27](=[O:28])[CH2:26][N:14]3[CH2:15][CH2:16][C:9]4[C:10](=[N:11][CH:12]=[C:7]([N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)[N:8]=4)[CH2:13]3)[CH2:30][CH2:31]2)[CH2:38][CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 574205621-(Chloroacetyl)-4-cyclobutylpiperazineHCID 574205822-Morpholin-4-yl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine

Product 1

HCID 574205816-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-2-morpholin-4-yl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-morpholin-4-yl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine (60 mg, 0.27 mmol) in acetonitrile (5 mL) is added NaI (50 mg, 0.333 mmol), K2CO3 (200 mg, 1.45 mmol) and 2-chloro-1-(4-cyclobutyl-piperazin-1-yl)-ethanone (100 mg, 0.463 mmol). The mixture is stirred overnight at rt. The mixture is diluted with DCM (25 mL) and filtered through Celite. The filtrate is concentrated and the residue is purified by PTLC eluting with EtOAc/MeOH/NEt3 (90:10:10) to yield the title compound. 1H NMR (300 MHz, CDCl3) δ 7.90 (1H, s), 3.85 (2H, m), 3.72 (4H, m), 3.63-3.60 (4H, m), 3.50 (2H, t), 3.40 (2H, s), 2.92-2.87 (3H, m), 2.74-2.69 (2H, m), 2.51 (2H, t), 2.34-2.26 (4H, m), 2.09-1.67 (m, 6H); MS (+VE) m/z 401.26 (M++1).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate is concentrated
  3. customthe residue is purified by PTLC
  4. washeluting with EtOAc/MeOH/NEt3 (90:10:10)

Sources & evidence

ORD record
ord-efe90e86ae5644d8a3af1f59b03e55f7
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

Loading…