Hydrochloric Acid → (S)-1-(5-(5-(cyclopropylmethylthio)-3-(2-methylpyridin-3-yloxy)-pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol

HRID 534020Notes

Reaction equation

[CH:1]1([CH2:4][S:5][C:6]2[CH:7]=[C:8]([O:28][C:29]3[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=3)[C:9]([NH:12][C:13]3[S:17][N:16]=[C:15]([C@H:18]4[CH2:22][O:21]C5(CCCCC5)[O:19]4)[N:14]=3)=[N:10][CH:11]=2)[CH2:3][CH2:2]1.Cl>C(O)C>[CH:1]1([CH2:4][S:5][C:6]2[CH:7]=[C:8]([O:28][C:29]3[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=3)[C:9]([NH:12][C:13]3[S:17][N:16]=[C:15]([C@H:18]([OH:19])[CH2:22][OH:21])[N:14]=3)=[N:10][CH:11]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (S)-N-(5-(cyclopropylmethylthio)-3-(2-methylpyridin-3-yloxy)-pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decane-2-yl)-1,2,4-thiadiazol-5-amine (0.30 g, 0.586 mmol) in ethanol (20 mL) was added 1 M HCl (0.87 mL) and the reaction heated to 80° C. for 2 hours. The reaction was cooled and concentrated in vacuo and the solid triturated with ethanol The solid was dried in vacuo to afford (S)-1-(5-(5-(cyclopropylmethylthio)-3-(2-methylpyridin-3-yloxy)-pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol (0.146 g, 0.338 mmol, 57.7% yield) as the mono HCl salt. Mass Spectrum (apci) m/z=432.0 (M+H−HCl).

Workup

temperatureThe reaction was cooled
concentrationconcentrated in vacuo
customthe solid triturated with ethanol The solid
customwas dried in vacuo

Sources & evidence

ORD record: ord-5cf36c745bd34df4b06d621aa2b30959
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853409B2

Reaction notes

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