4-(4-Methylpiperazino)-1,2-benzenediamine → HCID 136168706, compound

HRID 2274429Notes

Reaction equation

HRID 2274429 reaction equation
[N+:1]([C:4]1[C:5]([CH:15]=O)=[N:6][N:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:8]=1)([O-:3])=[O:2].[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:25]=[C:26]([NH2:31])[C:27]([NH2:30])=[CH:28][CH:29]=2)[CH2:20][CH2:19]1>CO>[CH3:17][N:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:29]=[CH:28][C:27]3[N:30]=[C:15]([C:5]4[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][N:7]([CH:9]5[CH2:14][CH2:13][CH2:12][CH2:11][O:10]5)[N:6]=4)[NH:31][C:26]=3[CH:25]=2)[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 27635454-(4-Methylpiperazino)-1,2-benzenediamineHCID 224778374-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde

Product 1

HCID 136168706HCID 136168706, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

742 mg of 4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazole-3-carbaldehyde are added to a solution of 680 mg of 4-(4-methylpiperazino)-1,2-benzenediamine in 30 mL of methanol. The reaction medium is stirred at 22° C. for 3 hours. The reaction medium is heated at 60° C. using an oil bath for 1H30, and then stirred at 22° C. for 64 hours. After evaporation, the reaction crude is purified by flash chromatography on an Intelliflash apparatus on an Analogix RS-12 cartridge. The elution is carried out in dichloromethane containing 10% methanol. 370 mg of 6-(4-methylpiperazin-1-yl)-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzimidazole are isolated. Analytical LC/MS: tr=1.88 min; [M+H]+=412.32; ELSD=97%; DAD=93%. 1H NMR (400 MHz, DMSO-d6, δ in ppm): 1.50 to 2.23 (m, 6H); 2.25 (s, 3H); 2.50 (m masked, 4H); 3.14 (m, 4H); 3.70 (m, 1H); 4.00 (m, 1H); 5.59 (broad d, J=9.5 Hz, 1H); from 6.90 to 7.15 (m, 2H); from 7.39 to 7.54 (m, 1H); 9.17 (s, 1H); from 12.5 to 12.7 (m, 1H).

Workup

  1. temperatureThe reaction medium is heated at 60° C.
  2. stirringstirred at 22° C. for 64 hours
  3. customAfter evaporation
  4. customthe reaction crude
  5. customis purified by flash chromatography on an Intelliflash apparatus on an Analogix RS-12 cartridge
  6. washThe elution

Sources & evidence

ORD record
ord-99a8f2ef124f4b98a055ff9de94a0b4f
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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