Chlorosuccinimide → HCID 89781889, compound

HRID 1056237Notes

Reaction equation

HRID 1056237 reaction equation
[CH3:1][C:2]1[C:11]([NH:12][C:13]2([CH3:16])[CH2:15][CH2:14]2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:17]2[NH:21][C:20]3[CH2:22][NH:23][C:24](=[O:25])[C:19]=3[CH:18]=2)[N:3]=1.[Cl:26]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:26][C:18]1[C:19]2[C:24](=[O:25])[NH:23][CH2:22][C:20]=2[NH:21][C:17]=1[C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[N:10]=[C:11]([NH:12][C:13]1([CH3:16])[CH2:15][CH2:14]1)[C:2]([CH3:1])=[N:3]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 89783535HCID 89783535, compound

Product 1

HCID 89781889HCID 89781889, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 25-mL round-bottomed flask was added 2-(2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (357) (68 mg, 0.20 mmol), N-chlorosuccinimide (33 mg, 0.24 mmol) (Alfa-Aesar, Ward Hill, Mass.), and CHCl3 (3 mL). The reaction mixture was stirred at RT for 16 h and partitioned between water (5 mL) and EtOAc (5 mL). The organic extract was washed with brine (5 mL), dried over Na2SO4, and concentrated. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0-3% MeOH in DCM to provide 3-chloro-2-(2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (358) (9 mg, 12% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 13.75 (s, 1H), 8.40 (dd, J=1.27, 7.73 Hz, 1H), 7.75 (s, 2H), 7.70 (dd, J=1.27, 8.12 Hz, 1H), 7.44 (t, J=7.82 Hz, 1H), 4.32 (s, 2H), 2.51 (s, 3H), 1.45 (s, 3H), 0.90-0.95 (m, 2H), 0.73-0.79 (m, 2H). m/z (ESI, +ve) 368.1 (M+H)+.

Workup

  1. custompartitioned between water (5 mL) and EtOAc (5 mL)
  2. extractionThe organic extract
  3. washwas washed with brine (5 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material was absorbed onto a plug of silica gel
  7. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (12 g)
  8. washeluting with a gradient of 0-3% MeOH in DCM

Sources & evidence

ORD record
ord-2099cf1eb86d4cf7ae22315812d607d8
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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