Cyclopropylamine → 9-Bromo-5-cyclopropylcarbamoyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52496Notes

Reaction equation

HRID 52496 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([C:17](O)=[O:18])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH:20]1([NH2:23])[CH2:22][CH2:21]1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([C:17](=[O:18])[NH:23][CH:20]3[CH2:22][CH2:21]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 69828CyclopropylamineHCID 99053359-bromo-5-carboxy-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 540060779-Bromo-5-cyclopropylcarbamoyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 93%

Procedure

A procedure similar to that described in Example 5 was carried out with 9-bromo-5-carboxy-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (300 mg, 0.92 mmol) and cyclopropylamine (100 μL, 1.0 mmol) to give 310 mg of the title compound (93%): mp 222°~225° C.; 1H NMR (270 MHz, DMSO-d6) δ12.13 (s, 1H), 8.22 (d, 1H, J=4.0 Hz), 7.18 (bs, 1H), 7.16 (bs, 1H), 5.02~5.06 (m, 1H), 2.79 (dm, 1H, J=16.8 Hz), 2.45~2.62 (m, 2H), 2.36 (dm, 1H, J=13.5 Hz), 1.81~1.97 (m, 1H), 0.62 (dm, 2H, J=7.2 Hz), 1.33~1.41 (m, 2H).

Sources & evidence

ORD record
ord-85b68172f6b34ba3a6a0502c336fc6ef
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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