Pyridine → (S)-N-(5-bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-amine

HRID 1523543Notes

Reaction equation

CS(O[N:6]=[C:7](Cl)[C@H:8]1[CH2:12][O:11][C:10]2([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[O:9]1)(=O)=O.N1C=CC=CC=1.[S-:25][C:26]#[N:27].[Na+].[Br:29][C:30]1[CH:31]=[C:32]([O:37][C:38]2[C:39]([CH3:44])=[N:40][CH:41]=[CH:42][CH:43]=2)[C:33]([NH2:36])=[N:34][CH:35]=1>C(#N)C>[Br:29][C:30]1[CH:31]=[C:32]([O:37][C:38]2[C:39]([CH3:44])=[N:40][CH:41]=[CH:42][CH:43]=2)[C:33]([NH:36][C:26]2[S:25][N:6]=[C:7]([C@H:8]3[CH2:12][O:11][C:10]4([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]4)[O:9]3)[N:27]=2)=[N:34][CH:35]=1

Participants

Conditions

Temperature: 40 °C

Procedure

(R)—N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride (1.86 g, 6.25 mmol), pyridine (1.13 g, 14.3 mmol) and sodium thiocyanate (0.58 g, 7.14 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 (1.0 g, 3.57 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 (S)—N-(5-bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-amine (0.90 g, 1.78 mmol, 50% yield) as a white solid.

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-a06a51d3be4f4fe7ac02074fff1f7107
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079890B2

Reaction notes

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