5-Chloro-3-methylbenzene-1,2-diamine → 6-Chloro-4-methyl-2-{4-methyl-6-[3-(1-methyl-piperidin-4-yl)-propoxy]-pyridin-3-yl}-1H-benzoimidazole

HRID 2114474Notes

Reaction equation

HRID 2114474 reaction equation
CC1C2N=C(C3C=NC(OCCCC4CCN(C)CC4)=CC=3)NC=2C=CC=1.[CH3:28][C:29]1[CH:34]=[C:33]([O:35][CH2:36][CH2:37][CH2:38][CH:39]2[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]2)[N:32]=[CH:31][C:30]=1[CH:46]=O.[Cl:48][C:49]1[CH:54]=[C:53]([NH2:55])[C:52]([NH2:56])=[C:51]([CH3:57])[CH:50]=1>>[Cl:48][C:49]1[CH:50]=[C:51]([CH3:57])[C:52]2[N:56]=[C:46]([C:30]3[CH:31]=[N:32][C:33]([O:35][CH2:36][CH2:37][CH2:38][CH:39]4[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]4)=[CH:34][C:29]=3[CH3:28])[NH:55][C:53]=2[CH:54]=1

Participants

4

Reactant 3

HCID 15125155-Chloro-3-methylbenzene-1,2-diamineHCID 112799924-Methyl-2-{6-[3-(1-methyl-piperidin-4-yl)-propoxy]-pyridin-3-yl}-1H-benzoimidazoleHCID 575254564-Methyl-6-[3-(1-methyl-piperidin-4-yl)-propoxy]-pyridine-3-carbaldehyde

Product 1

HCID 114298666-Chloro-4-methyl-2-{4-methyl-6-[3-(1-methyl-piperidin-4-yl)-propoxy]-pyridin-3-yl}-1H-benzoimidazoleYield 30%

Procedure

4-Methyl-2-{6-[3-(1-methyl-piperidin-4-yl)-propoxy]-pyridin-3-yl}-1H-benzoimidazole. This compound was prepared by the method described in General Procedure 3 using 4-methyl-6-[3-(1-methyl-piperidin-4-yl)-propoxy]-pyridine-3-carbaldehyde (60 mg, 0.22 mmol, 1.0 equiv), 5-chloro-3-methyl-benzene-1,2-diamine (34 mg, 0.22 mmol, 1.0 equiv) and Na2S2O5 (54 mg, 0.29 mmol, 1.3 equiv). Purification by Method 2 afforded 27 mg (30%) of the title compound. MS (electrospray): mass calculated for C23H29ClN4O, 412.20; m/z found, 413.4 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.77 (s, 1H), 8.23 (dd, J=8.7, 2.3 Hz, 1H), 7.25 (m, 1H), 7.12 (t, J=7.5 Hz, 1H), 7.04-6.98 (m, 1H), 6.74 (d, J=8.7 Hz, 1H), 4.34 (t, J=6.6 Hz, 2H), 2.84-2.76 (m, 2H), 2.73-2.34 (br s, 3H), 2.23 (s, 3H), 1.92-1.83 (m, 2H), 1.81-1.62 (m, 4H), 1.39-1.17 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-aefe13d89a2146b0b8e6bc6069f781fa
Source dataset
uspto-grants-2008_10
Patent number
US07432378B2

Reaction notes

Loading…