Triethylamine → HCID 10223000, compound

HRID 1282297Notes

Reaction equation

HRID 1282297 reaction equation
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:18][O:19][C:20]1[C:29]([O:30][CH3:31])=[N:28][C:27]2[C:26]([C:32](Cl)=[O:33])=[C:25]([CH3:35])[C:24]([N+:36]([O-:38])=[O:37])=[CH:23][C:22]=2[N:21]=1>O1CCCC1>[C:2]([O:6][C:7](=[O:10])[CH2:8][NH:9][C:32]([C:26]1[C:27]2[N:28]=[C:29]([O:30][CH3:31])[C:20]([O:19][CH3:18])=[N:21][C:22]=2[CH:23]=[C:24]([N+:36]([O-:38])=[O:37])[C:25]=1[CH3:35])=[O:33])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 10805016HCID 10805016, compound

Product 1

HCID 10223000HCID 10223000, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of glycine tert-butyl ester hydrochloride 104 mg (0.67 mmol) and triethylamine in 3 mL anhydrous tetrahydrofuran 0.26 mL (1.69 mmol) under an atmosphere of nitrogen was added dropwise a solution of 2,3-dimethoxy-6-methyl-7-nitro-quinoxaline-5-carbonyl chloride (13) 200 mg (0.64 mmol) in 7 mL anhydrous tetrahydrofuran at 0° C. After the addition was complete (approximately 5 minutes), the reaction mixture was stirred at room temperature for 24 hours, filtered, and concentrated. The residue was taken up in ethyl acetate and the organic solution was washed with water, saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated. The crude product was purified by elution through a flash column (silica gel 60, 230-400 mesh, 3:2 hexanes/ethyl acetate) to give a yellow oil which crystallized on standing, 200 mg (77%), mp 125-126° C.; 1H NMR (CDCl3): δ 8.32 (s, 1H, 8-H), 6.32 (br s, 1H, amide NH), 4.14 (d, 2H, J=5.1 Hz), 4.09 (s, 3H), 3.99 (s, 3H), 2.54 (s, 3H), 1.47 (s, 9H, tert-butyl protons); MS (APCI): m/z 407 (M+H). Anal. Calcd. for C18H22N4O7: C, 53.20; H, 5.46; N, 13.79. Found: C, 53.24; H, 5.45; N, 13.55.

Workup

  1. additionAfter the addition
  2. custom(approximately 5 minutes)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washthe organic solution was washed with water, saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by elution through a flash column (silica gel 60, 230-400 mesh, 3:2 hexanes/ethyl acetate)
  10. customto give a yellow oil which
  11. customcrystallized

Sources & evidence

ORD record
ord-7a9bc3fc8a0f4378b781e8f288e4d745
Source dataset
uspto-grants-2002_09
Patent number
US06455698B1

Reaction notes

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