Hydrochloric Acid → 8-Bromo-5-benzylcarbamoyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

HRID 52467Notes

Reaction equation

HRID 52467 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([C:16]([OH:18])=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([C:16](=[O:18])[NH:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[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

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 99955808-Bromo-5-carboxy-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 199632378-Bromo-5-benzylcarbamoyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dioneYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-bromo-5-carboxy-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione (300 mg, 0.96 mmol) and benzylamine (114 mg, 1.06 mmol) in DMF (3 mL) was added 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide (164 mg, 1.06 mmol) and N-hydroxybenztriazole (162 mg, 1.06 mmol) at 0° C. The mixture was stirred at room temperature overnight and aqueous 0.1N HCl was added. The precipitates formed were collected by filtration, washed with distilled water, and dried in vacuo to give 384 mg of the title compound (99%): mp 152.5°~153° C.; 1H NMR (270 MHz, DMSO-d6) δ12.01 (s, 1 H), 11.52 (t, 1H, J=5.6 Hz), 7.34 (m, 5H), 7.21 (d, 1H, J=1 Hz), 7.07 (d, 1H, J=1 Hz), 5.17 (dd, 1H, J=17, 10 Hz), 4.32 (d, 2H, J=5.6 Hz), 3.74 (dd, 1H, J=17, 10 Hz), 3.20 (dd, 1H, J=17, 5 Hz).

Workup

  1. customThe precipitates formed
  2. filtrationwere collected by filtration
  3. washwashed with distilled water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2801dba1468b4e529c4a6955896b1b20
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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