Hydrochloric Acid → 9-Bromo-5-[(p-aminomethylphenyl)carbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochloride

HRID 52553Notes

Reaction equation

HRID 52553 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:35])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][NH:27]C(OC(C)(C)C)=O)=[CH:22][CH:21]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[ClH:36]>C1COCC1.O1CCOCC1>[ClH:36].[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:35])[NH:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][NH2:27])=[CH:24][CH:25]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 539471179-Bromo-5-[(p-tert-butoxycarbonylaminomethylphenyl)carbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 678860589-Bromo-5-[(p-aminomethylphenyl)carbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochlorideYield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 9-bromo-5-[(p-tert-butoxycarbonylaminomethylphenyl)carbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (180 mg, 0.3 mmol) in THF (6 mL) was added 4N HCl in dioxane (6 mL). The mixture was stirred for 3 h at room temperature and concentrated. The residue was collected by filtration, washed with diethyl ether, and dried in vacuo to give 140 mg of the title compound (97%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.11 (s, 1H), 10.27 (s, 1H), 8.27 (bs, 2H), 7.61 (d, 2H, J=8.6 Hz), 7.40 (d, 2H, J=8.6 Hz), 7.23 (bs, 1H), 7.20 (bs, 1H), 5.17~5.26 (m, 1H), 3.96 (br, 2H), 3.10 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=17.1 Hz), 2.56~2.71 (m, 2H), 2.09 (dm, 1H, J=13.5 Hz), 1.82~1.96 (m, 1H).

Workup

  1. concentrationconcentrated
  2. filtrationThe residue was collected by filtration
  3. washwashed with diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4fbda584626045fe9d245039f74047e8
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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