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

HRID 1523631Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][S:5][C:6]1[CH:7]=[C:8]([O:28][C:29]2[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=2)[C:9]([NH:12][C:13]2[S:17][N:16]=[C:15]([C@H:18]3[CH2:22][O:21]C4(CCCCC4)[O:19]3)[N:14]=2)=[N:10][CH:11]=1.[ClH:36]>CCO>[ClH:36].[CH3:1][O:2][CH2:3][CH2:4][S:5][C:6]1[CH:7]=[C:8]([O:28][C:29]2[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=2)[C:9]([NH:12][C:13]2[S:17][N:16]=[C:15]([C@H:18]([OH:19])[CH2:22][OH:21])[N:14]=2)=[N:10][CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(S)—N-(5-(2-methoxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-amine (1.9 g, 3.68 mmol) was dissolved in EtOH (50 mL) and 6M HCl (3 mL) added and heated to 60° C. for 1.5 hours. The reaction was cooled to ambient temperature and partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate, extracted with CH2Cl2, dried, filtered and concentrated. The residue was purified over silica gel (0 to 10% methanol in EtOAc) to afford (S)-1-(5-(5-(2-methoxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol hydrochloride (1.13 g, 2.39 mmol, 65.0% yield) as a white solid after HCl salt formation. Mass Spectrum (apci) m/z=436.1 (M+H−HCl).

Workup

temperatureThe reaction was cooled to ambient temperature
custompartitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
extractionextracted with CH2Cl2
customdried
filtrationfiltered
concentrationconcentrated
customThe residue was purified over silica gel (0 to 10% methanol in EtOAc)

Sources & evidence

ORD record: ord-d373ea8339bb4dc182701fc4b73b46c7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079890B2

Reaction notes

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