3,4-Dimethylbenzene-1,2-diamine → 4,5-Dimethyl-2-{3-methyl-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-1H-benzoimidazole

HRID 646989Notes

Reaction equation

HRID 646989 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)[CH:5]=O.[CH3:21][C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[C:24]([NH2:29])[C:23]=1[NH2:30]>>[CH3:21][C:22]1[C:23]2[N:30]=[C:5]([C:4]3[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]4[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]4)=[C:2]([CH3:1])[CH:3]=3)[NH:29][C:24]=2[CH:25]=[CH:26][C:27]=1[CH3:28]

Participants

3

Reactant 2

HCID 5210773,4-Dimethylbenzene-1,2-diamineHCID 575254273-Methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde

Product 1

HCID 117497024,5-Dimethyl-2-{3-methyl-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-1H-benzoimidazoleYield 75.3%

Procedure

This compound was prepared by the method described in Example 1, using 3-methyl-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-benzaldehyde (180 mg, 0.65 mmol, 1.0 equiv), 3,4-dimethyl-benzene-1,2-diamine (89 mg, 0.65 mmol, 1.0 equiv), and Na2S2O5 (161 mg, 0.85 mmol, 1.3 equiv) in General Procedure 3. Purification by Method 2 afforded 192 mg (75%) of the title compound. MS (electrospray): mass calculated for C24H32N4O, 392.26; m/z found, 393.5 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.95-7.85 (m, 2H), 7.35-7.23 (m, 1H), 7.08-7.00 (m, 2H), 4.12 (t, J=6.0 Hz, 2H), 2.64-2.37 (m, 16H), 2.29 (s, 6H), 2.10-2.00 (m, 2H).

Workup

  1. customThis compound was prepared by the method
  2. customPurification by Method 2

Sources & evidence

ORD record
ord-2a497b4251c441449fa13f8ab84b8cd0
Source dataset
uspto-grants-2010_04
Patent number
US07705143B2

Reaction notes

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