HCID 59784370, compound → 2,3-Diamino-N-{4-[2-(4-methyl-piperazin-1-yl)-ethyl]-phenyl}-benzamide

HRID 470347Notes

Reaction equation

HRID 470347 reaction equation
[NH2:1][C:2]1[C:25]([N+:26]([O-])=O)=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[CH:9][CH:8]=1)=[O:5]>CO.[Pd]>[NH2:1][C:2]1[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)=[CH:11][CH:12]=1)=[O:5]

Participants

4

Reactant 1

HCID 59784370HCID 59784370, compound

Product 1

HCID 597844212,3-Diamino-N-{4-[2-(4-methyl-piperazin-1-yl)-ethyl]-phenyl}-benzamideYield 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-amino-N-{4-[2-(4-methyl-piperazin-1-yl)-ethyl]-phenyl}-3-nitro-benzamide (300 mg, 0.78 mmol) in MeOH (100 mL) were added Pd/C (10%, 30 mg) and the mixture was stirred under atmospheric hydrogen (balloon) at the room temperature for 1 h. The reaction mixture was filter over Celite to afford the title compound (261 mg, 94%). 1H NMR (MeOH-d4) δ 2.39 (s, 3H), 2.55-2.83 (12H), 6.62 (dd, J=9 Hz and 9 Hz, 1H), 6.86 (d, J=9 Hz, 1H), 7.08 (d, J=9 Hz, 1H), 7.22 (d, J=9 Hz, 2H), 7.54 (d, J=9 Hz, 2H). ESI-MS m/z 354.3 (MH+).

Workup

  1. filtrationThe reaction mixture was filter over Celite

Sources & evidence

ORD record
ord-4b6cf7b22a004b33aa9bc0360f7fecfb
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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