6-chloro-7-(4-methyl-piperazin-1-yl)-8-nitro-9H-beta-carboline → 6-chloro-7-(4-methyl-piperazin-1-yl)-8-amino-9H-beta-carboline

HRID 552182Notes

Reaction equation

HRID 552182 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:22]([O-])=O)[C:14]=1[N:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:22])[C:14]=1[N:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

4

Reactant 1

HCID 671656266-chloro-7-(4-methyl-piperazin-1-yl)-8-nitro-9H-beta-carboline

Product 1

HCID 671667376-chloro-7-(4-methyl-piperazin-1-yl)-8-amino-9H-beta-carbolineYield 55.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Suspended 236 mg of 6-chloro-7-(4-methyl-piperazin-1-yl)-8-nitro-9H-β-carboline in 100 ml of methanol and added 10% Pd/C (48 mg) under argon. The flask was flushed with hydrogen (3×) and the reaction mixture was stirred under a hydrogen atmosphere at RT overnight. The reaction mixture was filtered and Pd/C was removed using a pad of celite. The reaction mixture was evaporated to remove solvent and purified by flash chromatography to give 119 mg (55% yield) of the desired 6-chloro-7-(4-methyl-piperazin-1-yl)-8-amino-9H-β-carboline. 1H-NMR (300 MHz, methanol-d4): δ 2.39 (s, 3H), 2.46 (m, 2H), 2.87 (m, 4H), 3.83 (m, 2H), 7.50 (s, 1H), 7.97 (d, 1H), 8.24 (d, 1H), 8.78 (s, 1H). Retention Time (LC, method: ammonium acetate polar): 1.32 min. MS (M+H+): 316.

Workup

  1. customThe flask was flushed with hydrogen (3×)
  2. filtrationThe reaction mixture was filtered
  3. customPd/C was removed
  4. customThe reaction mixture was evaporated
  5. customto remove solvent
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1552e53d80c24af7981ecb126afc50bc
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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