Hydrochloric Acid → (S)-2-methyl-1-(5-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)propane-1,2-diol hydrochloride

HRID 1523653Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:9]=[C:10]([O:29][C:30]2[C:31]([CH3:37])=[N:32][N:33]([CH3:36])[C:34]=2[CH3:35])[C:11]([NH:14][C:15]2[S:19][N:18]=[C:17]([C@H:20]3[C:24]([CH3:26])([CH3:25])[O:23]C(C)(C)[O:21]3)[N:16]=2)=[N:12][CH:13]=1.[ClH:38]>C(O)C>[ClH:38].[CH3:26][C:24]([OH:23])([CH3:25])[C@H:20]([C:17]1[N:16]=[C:15]([NH:14][C:11]2[C:10]([O:29][C:30]3[C:31]([CH3:37])=[N:32][N:33]([CH3:36])[C:34]=3[CH3:35])=[CH:9][C:8]([S:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:13][N:12]=2)[S:19][N:18]=1)[OH:21]

Participants

Conditions

Temperature: 75 °C

Procedure

A flask was charged with (S)—N-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)-1,2,4-thiadiazol-5-amine (0.233 g, 0.432 mmol), ethanol (10 mL), and 3M HCl (0.288 ml, 0.863 mmol). The reaction was heated to 75° C. for 1 hour and then concentrated in vacuo. Ether was added to the residue and the mixture was stirred for 2 minutes to precipitate the product. The mixture was decanted and the resulting solids were dried in vacuo to afford (S)-2-methyl-1-(5-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)propane-1,2-diol hydrochloride (0.248 g, 0.387 mmol, 89.6% yield) as yellow solid. Mass Spectrum (apci) m/z=500.1 (M+H−HCl).

Workup

concentrationconcentrated in vacuo
additionEther was added to the residue
customto precipitate the product
customThe mixture was decanted
customthe resulting solids were dried in vacuo

Sources & evidence

ORD record: ord-9346811e7c8a4fd099720a7ecf73e269
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079890B2

Reaction notes

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