p-Toluenesulfonic acid monohydrate → HCID 58938133, compound

HRID 2246463Notes

Reaction equation

HRID 2246463 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[C:14]1[N:19]=[C:18]([C:20]#[N:21])[C:17]2[N:22]=[CH:23][N:24](C3CCCCO3)[C:16]=2[CH:15]=1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:11])[F:12])=[CH:6][C:5]=1[C:14]1[N:19]=[C:18]([C:20]#[N:21])[C:17]2[N:22]=[CH:23][NH:24][C:16]=2[CH:15]=1)[CH3:2]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58938120HCID 58938120, compound

Product 1

HCID 58938133HCID 58938133, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

6-(2-Ethoxy-5-trifluoromethyl-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-imidazo-[4,5-c]pyridine-4-carbonitrile (67 mg) and para-toluenesulfonic acid hydrate (10 mg) were added in methanol (5 ml) and DCM (5 ml). The mixture was stirred at room temperature overnight before concentration and purification on preparative HPLC to afford 6-(2-Ethoxy-5-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile. 1H NMR (MeOH) δ 8.55 (s, 1H) 8.48 (s, 1H) 8.15 (s, 1H) 7.70 (d, 1H) 7.29 (d, 1H) 4.26 (q, 2H) 1.46 (t, 3H) MS m/z 333.1 (m+1)

Sources & evidence

ORD record
ord-1e14072add9c464794900dc335d06e69
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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