HCID 10805016, compound → HCID 10202285, compound

HRID 1282299Notes

Reaction equation

HRID 1282299 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:9]([C:15](Cl)=[O:16])=[C:8]([CH3:18])[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]=2[N:4]=1.Cl.[C:23]([O:27][C:28](=[O:32])[CH2:29][CH2:30][NH2:31])([CH3:26])([CH3:25])[CH3:24]>>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:9]([C:15]([NH:31][CH2:30][CH2:29][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:32])=[O:16])=[C:8]([CH3:18])[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 10805016HCID 10805016, compoundHCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

Product 1

HCID 10202285HCID 10202285, compound

Procedure

Prepared from 2,3-dimethoxy-6-methyl-7-nitro-quinoxaline-5-carbonyl chloride (13) 250 mg (0.80 mmol) and β-alanine tert-butyl ester hydrochloride 153 mg (0.80 mmol). Reaction was continued for 2.5 hours, and the crude product was eluted through a flash column (3:2 hexanes:ethyl acetate), 230 mg (68%), mp 140-142° C., Rf 0.47 (1:1 hexanes:ethyl acetate); 1H NMR (CDCl3): δ 8.31 (s, 1H), 6.37 (br s, 1H), 4.08 (s, 3H), 3.97 (s, 3H), 3.74 (q, 2H, methylene protons, J=6.1 Hz), 2.57 (t, 2H, J=6.3 Hz, J=6.1 Hz), 2.55 (s, 3H), 1.42 (s, 9H); MS (APCI): m/z 421 (M+H). Anal. Calcd. for C19H24N4O7: C, 54.28; H, 5.75; N, 13.33. Found: C, 54.25; H, 5.69; N, 13.00.

Workup

  1. customReaction
  2. washthe crude product was eluted through a flash column (3:2 hexanes:ethyl acetate), 230 mg (68%), mp 140-142° C., Rf 0.47 (1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-c49c915bab544fb99cf53f3d8f518d99
Source dataset
uspto-grants-2002_09
Patent number
US06455698B1

Reaction notes

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