Phosphate → 9-Bromo-5-benzylaminomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochloride

HRID 52567Notes

Reaction equation

HRID 52567 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH:17]=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[ClH:19].[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([BH3-])#N.[Na+].P([O-])([O-])([O-])=O>CO>[ClH:19].[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][NH:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

6

Reactant 4

HCID 1061PhosphateHCID 2724127Benzylammonium chlorideHCID 5003444Sodium cyanoborohydrideHCID 541235619-Bromo-5-formyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 678865779-Bromo-5-benzylaminomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochlorideYield 41.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 9-bromo-5-formyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (154 mg, 0.5 mmol) and benzylamine hydrochloride (79 mg, 0.55 mmol)in methanol (3 mL) was added sodium cyanoborohydride (100 mg, 1.6 mmol) by portions at 0° C. The mixture was stirred for 4.5 h at 0° C. ~ room temperature and poured into 1/15M phosphate buffer (pH 7.4, 50 mL). The precipitates formed were collected by filtration and dried in vacuo. The solids were dissolved in dichloromethane and saturated hydrogen chloride in isopropanol was added. The resulting mixture was concentrated and the residual solid was rinsed with dichloromethane to give 90 mg of the title compound (41%): 1H NMR (270 MHz, DMSO-d6) δ12.13 (bs, 1H), 9.13 (s, 1H), 9.09 (s, 1H), 7.40~7.59 (m, 5H), 7.24 (d, 1H, J=2 Hz), 7.20 (d, 1H, J=2 Hz), 5.33~5.23 (m, 1H), 4.20 (d, 1H, J=13.0 Hz), 4.10 (d, 1H, J=13.0 Hz), 3.18~3.29 (m, 2H), 2.73~2.99 (m, 2H), 2.27 (dm, 1H, J=12.9 Hz), 1.77~2.00 (m, 1H).

Workup

  1. customThe precipitates formed
  2. filtrationwere collected by filtration
  3. customdried in vacuo
  4. dissolutionThe solids were dissolved in dichloromethane
  5. additionsaturated hydrogen chloride in isopropanol was added
  6. concentrationThe resulting mixture was concentrated
  7. washthe residual solid was rinsed with dichloromethane

Sources & evidence

ORD record
ord-8114d1de54374a30b2557fe57602d7b9
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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