Methyl 2-(4-aminophenyl)acetate → HCID 67885947, compound

HRID 52534Notes

Reaction equation

HRID 52534 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](O)=[O:19])[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]([CH2:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)=[O:24]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:30][C:29]3[CH:28]=[CH:27][C:26]([CH2:25][C:23]([O:22][CH3:21])=[O:24])=[CH:32][CH:31]=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 2761030Methyl 2-(4-aminophenyl)acetateHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 67885947HCID 67885947, compoundYield 81.2%

Procedure

A procedure similar to that described in Example 52 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (340 mg, 1 mmol) and p-methoxycarbonylmethylaniline (215 mg, 1.3 mmol) to give 395 mg of the title compound (81%): mp 262° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ10.02 (s, 1H), 7.50 (d, 2H, J=8.3 Hz), 7.23 (bs, 1H), 7.18 (d, 2H, J=8.3 Hz), 7.17 (bs, 1H), 5.17~5.26 (m, 1H), 3.61~3.62 (m, 5H), 3.06 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.84 (dm, 1H, J=17.1 Hz),2.56~2.66 (m, 2H), 2.11 (dm, 1H, J=13.5 Hz), 1.76~1.94 (m, 1H).

Sources & evidence

ORD record
ord-0804c569290d4ddaad01f483024e6b2c
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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