Ammonium Chloride → US10273222, Example 62

HRID 2277506노트

반응식

HRID 2277506 반응식
[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

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 904075092-(1-Methylimidazol-4-yl)pyridine-4-carbonitrile

생성물 1

HCID 90407594US10273222, Example 62수율 73%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-7fd09cc27d4f4677889b237ab9acd131
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133166B2

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