Benzylamine → HCID 178522854, compound

HRID 1168513Notes

Reaction equation

HRID 1168513 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:31])[C:12]3[C:13]4[N:14]([CH:30]=2)[CH2:15][C:16](=O)[NH:17][C:18]=4[CH:19]=[C:20]([CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:21]=3)=[O:9])=[CH:4][CH:3]=1.[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH2:34]([NH:41][C:16]1[CH2:15][N:14]2[CH:30]=[C:10]([C:8]([NH:7][CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:33][CH:32]=3)=[O:9])[C:11](=[O:31])[C:12]3[C:13]2=[C:18]([CH:19]=[C:20]([CH2:22][N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[CH:21]=3)[N:17]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 3010832HCID 3010832, compound

Product 1

HCID 178522854HCID 178522854, compound

Procedure

N-(4-Chlorobenzyl)-9-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide (Example 3, 30 mg) is heated under reflux with benzylamine (0.5 mL) for 18 h. The benzylamine is evaporated and the product is triturated with ether to give the title compound (18 mg), which is crystallized from ethyl acetate. Physical characteristics: M.p. 235-240° C.; 1H NMR (CDCl3) δ2.36, 3.51, 3.57, 4.55, 4.63, 7.2-7.5, 7.64, 8.20, 8.62, 10.5; HRMS m/z 555.2128 (C31H30ClN5O3).

Workup

  1. customThe benzylamine is evaporated
  2. customthe product is triturated with ether

Sources & evidence

ORD record
ord-024898fb29b34afa887f0481eda7da22
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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