3,4-dihydro-2H-pyran → 6-Chloro-2-tetrahydropyranyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246462Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]2[N:10]=[CH:11][NH:12][C:4]=2[CH:3]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.O.S(C1C=CC(C)=CC=1)(O)(=O)=O>C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]2[N:10]=[C:11]([CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][O:13]3)[NH:12][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

6-Chloro-1H-imidazo[4,5-c]pyridine-4-carbonitrile (1 g) was dissolved in ethyl acetate (20 ml). To above solution was added 3,4-dihydro-2H-pyran (1 ml) and tosylic acid hydrate (50 mg). The mixture was heated at 60° C. for 10 hours, than washed with sodium bicarbonate (5%, 10 mL). The organic layer dried over sodium sulphate, solvent removed to give the title compound. 1H NMR (DMSO) □ 8.92 (s, 1H), 8.30 s, 1H), 5.81 (d, 1H), 4.00 (m, 1H), 3.78 (m, 1H), 2.18 (m, 1H), 2.07 (m, 1H), 1.67 (m, 4H).

Workup

washthan washed with sodium bicarbonate (5%, 10 mL)
dry with materialThe organic layer dried over sodium sulphate, solvent
customremoved

Sources & evidence

ORD record: ord-230390ff91414e6fb1b7feaa46350c6d
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687515B2

Reaction notes

Loading…