3-Methoxyaniline → HCID 53681346, compound

HRID 52509Notes

Reaction equation

HRID 52509 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([OH:20])=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:20])[NH:26][C:25]3[CH:27]=[CH:28][CH:29]=[C:23]([O:22][CH3:21])[CH:24]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

3

Reactant 2

HCID 108243-MethoxyanilineHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 53681346HCID 53681346, compoundYield 96.8%

Procedure

A procedure similar to that described in Example 5 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (150 mg, 0.442 mmol) and m-methoxyaniline (76 mg, 0.62 mmol) to give 190 mg of the title compound (95%): mp 151°~154° C.; 1H NMR (270 MHz, DMSO-d6) δ12.07 (s, 1H), 10.00 (s, 1H), 7.27 (d, 1H, J=2 Hz), 7.24 (bs, 1H), 7.20 (t, 1H, J=8.1 Hz), 7.16 (bs, 1H), 6.64 (dd, 1H, J=8.1, 2 Hz), 6.88 (d, 2H, J =9 Hz), 5.16~5.17 (m, 1H), 3.72 (s, 3H), 3.05 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.82 (dm, 1H, J=16.8 Hz), 2.55~2.65 (m, 2H), 2.09 (dm, 1H, J=13.5 Hz), 1.80~1.96 (m, 1H).

Sources & evidence

ORD record
ord-08688c26a3644154b0c4e39ebb256245
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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