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

HRID 52500

Reaction equation

HRID 52500 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.[CH:21]1([NH2:24])[CH2:23][CH2:22]1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:20])[NH:24][CH:21]3[CH2:23][CH2:22]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 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 678858659-Bromo-5-cyclopropylcarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 86%

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, 0.44 mmol) and cyclopropylamine (50 μL, 0.5 mmol) to give 143 mg of the title compound (86%): mp 265°~268° C.; 1H NMR (270 MHz, DMSO-d6) δ12.04 bs, 1H), 8.04 (d, 1H, J=4 Hz), 7.20 (d, 1H, J=2 Hz), 7.14 (d, 1H, J=2 Hz), 5.05~5.14 (m, 1H), 2.97 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.77 (dm, 1H, J=17.1 Hz), 2.54~2.64 (m, 2H), 2.35 (dd, 1H, J=16.2, 4.5 Hz), 2.25 (dd, 1H, J=16.2, 11.7 Hz), 2.00 (dm, 1H, J=13.5 Hz), 1.73~1.87 (m, 1H), 0.56~0.64 (m, 2H), 0.32~0.41 (m, 2H).

Sources & evidence

ORD record
ord-05f7feb044bc43e79133901a555136c9
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Linked notes

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