Triethylamine → 2-[(1-aza-bicyclo[2.2.2]oct-3-ylamino)-methyl]-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246435Notes

Reaction equation

HRID 2246435 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.Cl.Cl.[NH2:29][CH:30]1[CH:35]2[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]2)[CH2:31]1.C(N(CC)CC)C>>[N:32]12[CH2:37][CH2:36][CH:35]([CH2:34][CH2:33]1)[CH:30]([NH:29][CH2:2][C:3]1[NH:4][C:5]3[CH:10]=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[C:13]([C:20]([F:23])([F:22])[F:21])[CH:12]=4)[N:8]=[C:7]([C:24]#[N:25])[C:6]=3[N:26]=1)[CH2:31]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 589381142-chloromethyl-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 589381262-[(1-aza-bicyclo[2.2.2]oct-3-ylamino)-methyl]-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrileYield 52.4%

Procedure

A solution of 2-chloromethyl-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (20 mg, 0.06 mmol), 3-aminoquinuclidine dihydrochloride (22.9 mg, 0.12 mmol) and triethylamine (18.2 mg, 0.18 mmol) in dimethylsulfoxide(500 μL) was heated in the Creator microwave at 120° C. for 5 minutes. The mixture was filtered and purified by preparative HPLC to afford 2-[(1-aza-bicyclo[2.2.2]oct-3-ylamino)-methyl]-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (14.8 mg) 1H NMR (MeOD) δ 8.34-8.27 (m, 3H) 7.29 (d, 2H) 4.95 (s, 2H) 4.29-4.21 (m, 3H) 4.00 (m, 1H) 3.86-3.69 (m 5H) 2.46 (m, 1H) 2.27-2.10 (m, 4H) 1.45 (t, 3H). MS m/z 471.8 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-db3991d72f924226a47b85f96d1f5f7b
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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