Ammonium Chloride → US10273222, Example 62

HRID 2277506Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][N:8]=2)[N:4]=[CH:3]1.[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([C:13]3[N:15]=[N:16][NH:17][N:14]=3)[CH:10]=[CH:9][N:8]=2)[N:4]=[CH:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-(1-methyl-1H-imidazol-4-yl)pyridine-4-carbonitrile (50 mg, 0.36 mmol) in 2 mL of DMF was added sodium azide (65 mg, 1 mmol) and ammonium chloride (54 mg, 1 mmol). The reaction mixture was heated at 90° C. for 20 hrs with vigorous stirring. It was then purified by ISCO flash column chromatography (MeOH/DCM=0-100%) to give the title compound as light pink solid (45 mg, 73%). 1H NMR (400 MHz, DMSO-d6): δ 3.73 (3H, s), 7.71 (1H, dd, J=1.5 Hz and 5.1 Hz), 7.74 (2H, s), 8.46 (1H, s), 8.51 (1H, d, J=5.0 Hz). [M+H] Calc'd for C10H9N7, 228. Found, 228.

Workup

customIt was then purified by ISCO flash column chromatography (MeOH/DCM=0-100%)

Sources & evidence

ORD record: ord-7fd09cc27d4f4677889b237ab9acd131
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133166B2

Reaction notes

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