Pyridine → HCID 135507203, compound

HRID 853660Notes

Reaction equation

HRID 853660 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:9](=[C:10]([OH:22])[C:11]4[N:12]=[CH:13][CH:14]=[N:15][C:16]=4[C:17]=3[OH:21])[C:8]2=[O:23])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34]>CN(C=O)C>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:8](=[O:23])[C:9]3[C:18](=[C:17]([OH:21])[C:16]4[N:15]=[CH:14][CH:13]=[N:12][C:11]=4[C:10]=3[O:22][C:33](=[O:34])[O:35][CH2:36][CH3:37])[C:19]2=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 178515144HCID 178515144, compound

Product 1

HCID 135507203HCID 135507203, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(4-Fluoro-benzyl)-5,9-dihydroxy-pyrrolo [3,4-g]quinoxaline-6,8-dione 242 (1 g, 2.95 mmol, 1 equiv.) was dissolved in DMF (30 ml, 0.1 M) and pyridine (477 μL, 5.89 mmol, 2 equiv.) before ethyl chloroformate was added (237 μL, 2.95 mmol, 1 equiv.). The reaction was stirred for 16 hours before being quenched with HCl (30 ml, 1 N) and extracted with ethyl acetate (2×30 mL). The organic layer washed several times with water (4×30 mL), saturated NaHCO3 (50 mL), brine solution (50 mL). It was dried over Na2SO4, filtered and concentrated in vacuo. Recrystallization was carried out in ethyl acetate and Hexanes to yield carbonic acid ethyl ester 7-(4-fluoro-benzyl)-9-hydroxy-6,8-dioxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoxalin-5-yl ester 243 as a light brown solid (98%, 1.20 g, 2.89 mmol). 1H NMR (300 MHz) CDCl3 δ 9.09 (d, J=6 Hz, 1 H), 8.97 (d, J=6 Hz, 1 H), 8.65 (bs, 1 H), 7.46 (d, J=4.8 Hz, 2 H), 7.03 (d, J=4.8 Hz, 2 H), 4.85 (s, 2 H), 4.04 (q, J=2.8 Hz, 2 H), 1.43 (q, J=2.8 Hz, 3 H). MS: 412.6 (M+1).

Workup

  1. custombefore being quenched with HCl (30 ml, 1 N)
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. washThe organic layer washed several times with water (4×30 mL), saturated NaHCO3 (50 mL), brine solution (50 mL)
  4. dry with materialIt was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customRecrystallization

Sources & evidence

ORD record
ord-e8246d5db9854d4bb23b6b61c076f854
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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