Pyridine → 1-(4-(5-(5-Bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone

HRID 1809595Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](Cl)=[N:11]OS(C)(=O)=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].N1C=CC=CC=1.[S-:24][C:25]#[N:26].[Na+].[Br:28][C:29]1[CH:30]=[C:31]([O:36][C:37]2[C:38]([CH3:43])=[N:39][CH:40]=[CH:41][CH:42]=2)[C:32]([NH2:35])=[N:33][CH:34]=1>C(#N)C>[Br:28][C:29]1[CH:30]=[C:31]([O:36][C:37]2[C:38]([CH3:43])=[N:39][CH:40]=[CH:41][CH:42]=2)[C:32]([NH:35][C:25]2[S:24][N:11]=[C:10]([CH:7]3[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH2:8]3)[N:26]=2)=[N:33][CH:34]=1

Participants

Conditions

Temperature: 40 °C

Procedure

1-acetyl-N-(methylsulfonyloxy)piperidine-4-carbimidoyl chloride (2.27 g, 8.03 mmol), pyridine (1.95 mL, 24.1 mmol) and sodium thiocyanate (0.651 g, 8.03 mmol) were dissolved in acetonitrile (45 mL). The solution was heated to 40° C. for 40 minutes. 5-bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-amine (1.50 g, 5.35 mmol) was added and the reaction was heated at 60° C. overnight. The solution was cooled to 0° C., filtered and the solid was dried to give 1-(4-(5-(5-bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone (2.63 g, 5.37 mmol, 100% yield) as a white solid. 1H NMR (CDCl3) δ 1.78-1.97 (m, 2H), 2.01-2.20 (m, 2H), 2.12 (s, 3H), 2.51 (s, 3H), 2.86 (t, 1H), 3.05-3.11 (m, 1H), 3.24 (t, 1H), 3.90 (d, 1H), 4.57 (d, 1H), 6.97 (d, 1H), 7.24-7.37 (m, 2H), 8.23 (d, 1H), 8.50 (d, 1H), 9.10 (bs, 1H).

Workup

temperaturethe reaction was heated at 60° C. overnight
temperatureThe solution was cooled to 0° C.
filtrationfiltered
customthe solid was dried

Sources & evidence

ORD record: ord-0ba32ca6dbd742919825f9ece73cead5
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362037B2

Reaction notes

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