Pyridine → 1,4-Dioxaspiro[4.5]decan-2-yl-1,2,4-thiadiazol-5-amine

HRID 533997Notes

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.[N:19]1C=CC=CC=1.[S-:25][C:26]#[N:27].[Na+].BrC1C=C(OC2C(C)=NC=CC=2)C(N)=NC=1>C(#N)C>[O:9]1[C:10]2([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[O:11][CH2:12][CH:8]1[C:7]1[N:6]=[C:26]([NH2:27])[S:25][N:19]=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-1558b255c35d429d82a05b1c51d93cad
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853409B2

Reaction notes

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