1-Methylpiperazine → 6-(4-ethoxy-3-trifluoromethyl-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246443Notes

Reaction equation

Cl[CH2:2][C:3]1[NH:4][C:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[C:13]([C:20]([F:23])([F:22])[F:21])[CH:12]=3)[N:8]=[C:7]([C:24]#[N:25])[C:6]=2[N:26]=1.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>CN(C=O)C.CO>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:8]=[C:7]([C:24]#[N:25])[C:6]3[N:26]=[C:3]([CH2:2][N:31]4[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]4)[NH:4][C:5]=3[CH:10]=2)=[CH:12][C:13]=1[C:20]([F:23])([F:22])[F:21])[CH3:19]

Participants

Conditions

Temperature: 120 °C

Procedure

2-Chloromethyl-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (20 mg, 0.053 mmol) was dissolved in DMF and N-methyl piperazine (26 mg, 0.26 mmol) was added. The mixture was heated to 120° C. for five minutes in a Smith Creator microwave. Mixture was diluted with methanol (4 ml) and loaded onto an SCX cartridge. Cartridge was washed three times with methanol (5 ml) then eluted with 2M methanolic ammonia. Methanolic ammonia was removed by evaporation under reduced pressure then mixture was prep HPLC purified to afford 8 mg of 6-(4-ethoxy-3-trifluoromethyl-phenyl)-2-(4-methyl-piperazin-1-ylmethyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile as a white solid. 1H NMR (MeOH) δ 8.28-8.20 (m, 2H), 8.13 (s, 1H), 7.26 (d, 1H), 4.22 (q, 2H), 3.92 (s, 2H), 2,67 (m, 8H), 2.38 (s, 3H), 1.45 (t, 3H). MS m/z 445.5 (M+1).

Workup

washCartridge was washed three times with methanol (5 ml)
washthen eluted with 2M methanolic ammonia
customMethanolic ammonia was removed by evaporation under reduced pressure
custompurified

Sources & evidence

ORD record: ord-92d20176ec4a4202919ae7a292a1b7d3
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687515B2

Reaction notes

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