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

HRID 646956Notes

Reaction equation

HRID 646956 reaction equation
ClC1C=C(OCCCN2CCN(C)CC2)C=CC=1[N:19]1[C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[C:27]([CH3:28])[C:22]=2[N:21]=C1.[Cl:30][C:31]1[CH:38]=[C:37]([O:39][CH2:40][CH2:41][CH2:42][N:43]2[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]2)[CH:36]=[CH:35][C:32]=1[CH:33]=O.CC1C(C)=CC=C(N)C=1N>CN(C=O)C>[Cl:30][C:31]1[CH:38]=[C:37]([O:39][CH2:40][CH2:41][CH2:42][N:43]2[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]2)[CH:36]=[CH:35][C:32]=1[C:33]1[NH:19][C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[C:27]([CH3:28])[C:22]=2[N:21]=1

Participants

5

Reactant 3

HCID 5210773,4-Dimethylbenzene-1,2-diamineHCID 575254242-Chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehydeHCID 86761058(2-Chloro-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-4,5-dimethyl-1H-benzoimidazole

Product 1

HCID 112584582-{2-Chloro-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-4,5-dimethyl-1H-benzoimidazoleYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{(2-Chloro-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-4,5-dimethyl-1H-benzoimidazole. 2-Chloro-4-[3-(4-methyl-piperazin-1-yl)-propoxy]-benzaldehyde (91.5 mg, 0.31 mmol, 1.0 equiv) and 3,4-dimethyl-benzene-1,2-diamine (42 mg, 0.31 mmol, 1.0 equiv) were stirred with Na2S2O5 (76 mg, 0.40 mmol, 1.3 equiv) in DMF (0.25 M) at 90° C. for 12 h. The reaction mixture was loaded directly on silica gel and purified according to Method 2, which afforded 98 mg (76%) of the title compound. MS (electrospray): mass calculated for C23H29ClN4O, 412.20. m/z found, 413.4 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.68 (br s, 1H), 7.33 (br s, 1H), 7.15 (d, J=2.5 Hz, 1H), 7.07 (d, J=8.7, 2.5 Hz, 1H), 7.03 (dd, J=8.7, 2.5 Hz, 1H), 4.13 (t, J=6.1 Hz, 2H), 2.60-2.39 (m, 13H), 2.39 (s, 3H), 2.30 (s, 3H), 2.05-1.95 (m, 2H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-a5d0eac2bb2e484fa3717d31a443fcf5
Source dataset
uspto-grants-2010_04
Patent number
US07705149B2

Reaction notes

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