Piperidine → 7-chloro-5-(hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)pyrido[4,3-b]pyrazine

HRID 57607Notes

Reaction equation

HRID 57607 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:19][CH:18]3[CH:14]([N:15](C(OCC4C5C=CC=CC=5C5C4=CC=CC=5)=O)[CH2:16][CH2:17]3)[CH2:13]2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[CH:3]=1.N1CCCCC1>C(Cl)Cl>[Cl:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:19][CH:18]3[CH:14]([NH:15][CH2:16][CH2:17]3)[CH2:13]2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86717380(9H-fluoren-9-yl)methyl 5-(7-chloropyrido[4,3-b]pyrazin-5-yl)hexahydropyrrolo[3,4-b]pyrrole-1 (2H)-carboxylate

Product 1

HCID 867173817-chloro-5-(hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)pyrido[4,3-b]pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (9H-fluoren-9-yl)methyl 5-(7-chloropyrido[4,3-b]pyrazin-5-yl)hexahydropyrrolo[3,4-b]pyrrole-1 (2H)-carboxylate (140 mg) and piperidine (2 mL) in CH2Cl2 (8 mL) was stirred at room temperature for 3 hours. The volatiles were removed under reduced pressure. The residue was treated with EtOAc/H2O, separated, and the aqueous solution was extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography to afford the title compound. MS (m/z): 276 (M+H)+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionThe residue was treated with EtOAc/H2O
  3. customseparated
  4. extractionthe aqueous solution was extracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-1c79fed0d72449fd96a997bb11ef8098
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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