6-(4-ethoxy-3-trifluoromethyl-phenyl)-2-(3-morpholin-4-yl-propenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile → 6-(4-Ethoxy-3-trifluoromethyl-phenyl)-2-(3-morpholin-4-yl-propyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246452Notes

Reaction equation

HRID 2246452 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([C:16]#[N:17])[C:13]3[N:18]=[C:19]([CH:21]=[CH:22][CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[NH:20][C:12]=3[CH:11]=2)=[CH:6][C:5]=1[C:30]([F:33])([F:32])[F:31])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([C:16]#[N:17])[C:13]3[N:18]=[C:19]([CH2:21][CH2:22][CH2:23][N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)[NH:20][C:12]=3[CH:11]=2)=[CH:6][C:5]=1[C:30]([F:33])([F:31])[F:32])[CH3:2]

Participants

4

Reactant 1

HCID 685148376-(4-ethoxy-3-trifluoromethyl-phenyl)-2-(3-morpholin-4-yl-propenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 589381246-(4-Ethoxy-3-trifluoromethyl-phenyl)-2-(3-morpholin-4-yl-propyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a flask containing a solution of 6-(4-ethoxy-3-trifluoromethyl-phenyl)-2-(3-morpholin-4-yl-propenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (16 mg) in ethanol was added 5% Pd/C (5 mg) and the vessel purged with hydrogen. The mixture was stirred for 1 h before filtration and purification by preparatice HPLC to afford the title compound. 1H NMR (MeOH) δ 8.32-8.25 (m, 2H) 8.17 (s, 1H) 7.30 (d, 1H) 4.24 (q, 2H) 4.20-3.84 (bm, 4H) 3.65-3.60 (bm, 2H) 3.40 (t, 2H) 3.22 (m, 4H) 2.40 (m, 2H) 1.45 (t, 3H) MS m/z 460.7 (m+1)

Workup

  1. customthe vessel purged with hydrogen

Sources & evidence

ORD record
ord-e95de9fddf2e4adb9d352fc41d99fb3a
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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