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

HRID 534055Notes

Reaction equation

[CH3:1][C:2]1[C:3]([S:8][C:9]2[CH:10]=[C:11]([O:31][C:32]3[C:33]([CH3:38])=[N:34][CH:35]=[CH:36][CH:37]=3)[C:12]([NH:15][C:16]3[S:20][N:19]=[C:18]([C@H:21]4[CH2:25][O:24]C5(CCCCC5)[O:22]4)[N:17]=3)=[N:13][CH:14]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[ClH:39]>C(O)C>[ClH:39].[CH3:1][C:2]1[C:3]([S:8][C:9]2[CH:10]=[C:11]([O:31][C:32]3[C:33]([CH3:38])=[N:34][CH:35]=[CH:36][CH:37]=3)[C:12]([NH:15][C:16]3[S:20][N:19]=[C:18]([C@H:21]([OH:22])[CH2:25][OH:24])[N:17]=3)=[N:13][CH:14]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (S)-N-(5-(3-methylpyridin-2-ylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decane-2-yl)-1,2,4-thiadiazol-5-amine (0.565 g, 1.03 mmol) in ethanol (25 mL) was added an aqueous solution of 6N HCl (2 mL). The reaction was heated at 80° C. for 2 hours, cooled to ambient temperature, stirred for 30 minutes, then cooled at 0° C. for an hour. The reaction was filtered, washed with cold ethanol, hexanes, and dried to afford (S)-1-(5-(5-(3-methylpyridin-2-ylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol hydrochloride (0.450 g, 0.891 mmol, 86.5% yield) as white crystals. Mass Spectrum (apci) m/z=469.1 (M+H−HCl).

Workup

temperaturecooled to ambient temperature
temperaturecooled at 0° C. for an hour
filtrationThe reaction was filtered
washwashed with cold ethanol, hexanes
customdried

Sources & evidence

ORD record: ord-2fbd45fac27d4714a6a02e02856b8409
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853409B2

Reaction notes

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