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

HRID 52549Notes

Reaction equation

HRID 52549 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=O)[NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[NH2:26])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[ClH:28]>C(#N)C>[ClH:28].[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]3[NH:26][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54379842HCID 54379842, compound

Product 1

HCID 678858059-Bromo-5-(2-benzimidazolylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochlorideYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 9-bromo-5-(o-aminophenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (Example 99) (250 mg, 0.5 mmol) in a mixture of acetonitrile (10 mL) and concentrated hydrochloric acid (2 mL) was heated at 50° C. for 5 h and concentrated. The residue was washed with distilled water and diethyl ether and dried in vacuo to give 150 mg of the title compound (73%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.15 (s, 1H), 7.80 (dd, 2H, J=6.3, 3 Hz), 7.54 (dd, 2H, J=6.3, 3 Hz), 7.28 (bs, 1H), 7.25 (bs, 1H), 5.26~5.35 (m, 1H), 3.41~3.50 (m, 2H), 3.07 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.90 (dm, 1H, J=17.1 Hz), 2.19 (dm, 1H, J=13.5 Hz), 1.90~2.05 (m, 1H).

Workup

  1. concentrationconcentrated
  2. washThe residue was washed with distilled water and diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a31991fea5f14131831f974de6bccc10
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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