Potassium Cyanide → HCID 54124339, compound

HRID 1459734Notes

Reaction equation

COS([O-])(=O)=O.[N:7]1([C:12]2[CH:13]=[C:14]3[C:20]([CH2:21][N+](C)(C)C)=[CH:19][NH:18][C:15]3=[CH:16][N:17]=2)[CH:11]=[N:10][CH:9]=[N:8]1.[C-:26]#[N:27].[K+]>O>[N:7]1([C:12]2[CH:13]=[C:14]3[C:20]([CH2:21][C:26]#[N:27])=[CH:19][NH:18][C:15]3=[CH:16][N:17]=2)[CH:11]=[N:10][CH:9]=[N:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N-([5-(1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]methyl-N,N,N-trimethylammonium methylsulphate (0.56 g, 1.5 mmol) in water (4ml) was added a solution of potassium cyanide (0.239 g, 3.7 mmol) in water (2ml). This mixture was heated at 70° C. for 1 h. Further potassium cyanide (80mg, 1.2 mmol) was added and the mixture heated for another hour at 70° C. Further potassium cyanide (80mg, 1.2 mmol) was added and the mixture heated at 70° C. for 1 hour and then at 100° C. for 20 min. The mixture was then cooled in ice for 30 min. The precipitate was collected by filtration and washed with water. The solid was chromatographed on silica eluting with 5% MeOH in DCM to afford the title compound (0.215 g, 63%) as a colourless solid; mp 218°-220° C. 1H NMR (250 MHz, d6 -DMSO) δ 4.19 (2H, s), 7.78 (1H, s), 8.12 (1H, s), 8.26 (1H, s), 8.71 (1H, s), 9.29 (1H, s), 11.93 (1H, br s).

Workup

temperaturethe mixture heated for another hour at 70° C
temperaturethe mixture heated at 70° C. for 1 hour
temperatureThe mixture was then cooled in ice for 30 min
filtrationThe precipitate was collected by filtration
washwashed with water
customThe solid was chromatographed on silica eluting with 5% MeOH in DCM

Sources & evidence

ORD record: ord-010bd918ec70402b9efaa62c138dc649
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854268

Reaction notes

Loading…