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1-(2-Hydroxyethyl)piperazine → 7-chloro-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)-1H,2H-pyrido[3,4-b]pyrazin-2-one

HRID 600287
Notes
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Reaction equation

HRID 600287 reaction equation
Cl[C:2]1[C:3](=[O:19])[N:4]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH3:18])[C:5]2[CH:11]=[C:10]([Cl:12])[N:9]=[CH:8][C:6]=2[N:7]=1.[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)CC)C>C1COCC1>[Cl:12][C:10]1[N:9]=[CH:8][C:6]2[N:7]=[C:2]([N:26]3[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][OH:20])[CH2:24][CH2:25]3)[C:3](=[O:19])[N:4]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH3:18])[C:5]=2[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 8471TriethylamineHCID 453799573,7-Dichloro-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one

Product 1

HCID 453800737-chloro-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)-1H,2H-pyrido[3,4-b]pyrazin-2-oneYield 83%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of 3,7-dichloro-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one (200 mg, 0.66 mmol), 1-(2-hydroxyethyl)piperazine (117 mg, 0.90 mmol, Aldrich) and triethylamine (0.27 mL, 1.94 mmol) in THF (3 mL) was stirred at room temperature for one hour. The reaction was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and solvent was removed at reduced pressure to give 7-chloro-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2(1H)-one. (218 mg, 83% yield). 1H NMR (CDCl3) δ 8.48 (1H), 7.34 (1H), 4.33-4.30 (2H), 4.04-4.00 (4H), 3.76-3.72 (2H), 3.69-3.65 (2H), 3.38-3.34 (2H), 2.67-2.64 (4H), 2.62-2.58 (2H), 1.55-1.48 (2H), 0.87-0.82 (3H).

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate, and solvent
  6. customwas removed at reduced pressure

Sources & evidence

ORD record
ord-8a8ab3d28a704494a866deae0b59b53e
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902195B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes