(2-Amino-3,5-dimethylphenyl)amine → 2-{2-Chloro-4-[3-(1-methyl-piperidin-4-yl)-propoxy]-phenyl}-4,6-dimethyl-1H-benzoimidazole

HRID 646967Notes

Reaction equation

HRID 646967 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([NH2:29])[C:23]=1[NH2:30]>>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:7]=[CH:6][C:3]=1[C:4]1[NH:29][C:24]2[CH:25]=[C:26]([CH3:28])[CH:27]=[C:22]([CH3:21])[C:23]=2[N:30]=1

Participants

3

Reactant 2

HCID 3613321(2-Amino-3,5-dimethylphenyl)amineHCID 575254252-Chloro-4-[3-(1-methyl-piperidin-4-yl)-propoxy]-benzaldehyde

Product 1

HCID 112584292-{2-Chloro-4-[3-(1-methyl-piperidin-4-yl)-propoxy]-phenyl}-4,6-dimethyl-1H-benzoimidazoleYield 87%

Procedure

This compound was prepared by the method described in Example 2, using 2-chloro-4-[3-(1-methyl-piperidin-4-yl)-propoxy]-benzaldehyde (106 mg, 0.36 mmol, 1.0 equiv), 3,5-dimethyl-benzene-1,2-diamine (49 mg, 0.36 mmol, 1.0 equiv), and Na2S2O5 (88 mg, 0.47 mmol, 1.3 equiv) in Step C. Purification by Method 2 afforded 128 mg (87%) of the title compound. MS (electrospray): mass calculated for C24H30ClN3O, 411.21. m/z found, 412.4 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.68 (d, J=8.5 Hz, 1H), 7.21 (br s, 1H), 7.12 (d, J=2.4 Hz, 1H), 7.01 (dd, J=8.7, 2.5 Hz, 1H), 6.90 (s, 1H), 4.05 (t, J=6.3 Hz, 2H), 2.92-2.88 (m, 2H), 2.54 (s, 3H), 2.43 (s, 3H), 2.29 (s, 3H), 2.09-2.03 (m, 2H), 1.85-1.76 (m, 4H), 1.47-1.11 (m, 5H).

Workup

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

Sources & evidence

ORD record
ord-ff4d9c994cff48bf8e6ee4d7d39e1a5a
Source dataset
uspto-grants-2010_04
Patent number
US07705149B2

Reaction notes

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