Pyridine → HCID 67485959, compound

HRID 534113Notes

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]([CH3:45])=[N:40][N:41]([CH3:44])[C:42]=2[CH3:43])[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]([CH3:45])=[N:40][N:41]([CH3:44])[C:42]=2[CH3:43])[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

A flask was charged with (R)-N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride (1.53 g, 5.15 mmol), pyridine (1.25 ml, 15.4 mmol), sodium thiocyanate (0.417 g, 5.15 mmol) and acetonitrile (15 mL). The solution was heated to 40° C. for 40 minutes. 5-Bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-amine (1.02 g, 3.43 mmol) was added and the reaction was heated to 70° C. overnight. The reaction was cooled to ambient temperature, partitioned between EtOAc and water, dried over sodium sulfate, filtered and concentrate. The residue was purified over silica gel (10% MeOH/EtOAc) to afford (S)-N-(5-Bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decane-2-yl)-1,2,4-thiadiazol-5-amine (1.66 g, 3.18 mmol, 92.7% yield) as a yellow solid.

Workup

temperaturethe reaction was heated to 70° C. overnight
temperatureThe reaction was cooled to ambient temperature
custompartitioned between EtOAc and water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrate
customThe residue was purified over silica gel (10% MeOH/EtOAc)

Sources & evidence

ORD record: ord-26ba52fb4d674c7cae1b2bd02df7e4d2
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853409B2

Reaction notes

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