3-(4-Methylpiperazin-1-yl)benzene-1,2-diamine → HCID 178494100, compound

HRID 470344Notes

Reaction equation

HRID 470344 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([O:16][CH3:17])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][C:3]=1[CH:4]=O.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[C:26]=2[NH2:32])[CH2:21][CH2:20]1>CC(N(C)C)=O>[CH3:17][O:16][C:11]1[C:10]([C:7]2[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([C:4]3[NH:32][C:26]4[C:25]([N:22]5[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]5)=[CH:30][CH:29]=[CH:28][C:27]=4[N:31]=3)[CH:6]=2)=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 218773413-(4-Methylpiperazin-1-yl)benzene-1,2-diamineHCID 59784178HCID 59784178, compound

Product 1

HCID 178494100HCID 178494100, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To mixture of 2-hydroxy-5-(2-methoxy-pyridin-3-yl)-benzaldehyde (57 mg, 0.25 mmol) and 3-(4-methyl-piperazin-1-yl)-benzene-1,2-diamine (51 mg, 0.25 mol) was added DMA (1 mL) and the resulting solution was stirred at the room temperature for 15 min, heated at 110° C. for 15 h open to the air, concentrated under reduced pressure. The residual crude was purified by chromatography (500:10:1 CH2Cl2/MeOH/28% aqueous NH4OH) to afford the title compound (10.8 mg, 10.5%). 1H NMR (MeOH-d4) δ 2.41 (s, 3H), 2.78 (m, 4H), 3.49 (m, 4H), 3.97 (s, 3H), 6.72 (m, 1H) 7.05-7.20 (4H), 7.56 (d, J=9 Hz, 1H), 7.78 (d, J=9 Hz, 1H), 8.10-8.13 (2H). ESI-MS m/z 416.5 (MH+).

Workup

  1. temperatureheated at 110° C. for 15 h open to the air
  2. concentrationconcentrated under reduced pressure
  3. customThe residual crude was purified by chromatography (500:10:1 CH2Cl2/MeOH/28% aqueous NH4OH)

Sources & evidence

ORD record
ord-b1f9923507be4a2289676a93c0497726
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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