Imidazo[1,2-a]pyridin-8-ylmethanol → HCID 178477910, compound
Reaction equation
O[CH2:2][C:3]1[C:4]2[N:5]([CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:12][C:13]1[CH:22]=[CH:21][C:16]2[N:17]=[C:18]([SH:20])[NH:19][C:15]=2[CH:14]=1>>[Cl:12][C:13]1[CH:22]=[CH:21][C:16]2[NH:17][C:18]([S:20][CH2:2][C:3]3[C:4]4[N:5]([CH:9]=[CH:10][N:11]=4)[CH:6]=[CH:7][CH:8]=3)=[N:19][C:15]=2[CH:14]=1Participants
3
Procedure
A solution of 20 g (0.12 mole) of 3-chloro-6-nitroaniline in 350 ml of methanol was hydrogenated over 5% palladium on carbon to yield 24.9 g of the corresponding diamino compound. Reaction of the diamino compound with potassium ethylxanthate using the method described in Example 10 yielded 19 g of 5-chloro-2-mercaptobenzimidazole, as confirmed by elemental analysis. The title compound (1.14 g) was prepared by the method of Example 6 using 8-hydroxymethylimidazo[1,2-a]pyridine as the hydrochloride salt (701 mg, 3.8 mmole) and using 701 mg (3.8 mmole) of 5-chloro-2-mercaptobenzimidazole instead of 2-mercapto-5-methoxybenzimidazole. Structure assignment was supported by the nmr and infrared spectra.
Sources & evidence
- ORD record
- ord-1cf71a1c5fb448e3a1a4c042114e077e
- Source dataset
- uspto-grants-1987_08
- Patent number
- US04687775
Reaction notes
Loading…