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

HRID 1523558Notes

Reaction equation

HRID 1523558 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[C:10]([NH:22][C:23]3[S:27][N:26]=[C:25]([C@H:28]4[CH2:32][O:31]C5(CCCCC5)[O:29]4)[N:24]=3)=[N:11][CH:12]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:14]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[ClH:38]>C(O)C>[ClH:38].[CH3:1][C:2]1[C:7]([O:8][C:9]2[C:10]([NH:22][C:23]3[S:27][N:26]=[C:25]([C@H:28]([OH:29])[CH2:32][OH:31])[N:24]=3)=[N:11][CH:12]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:14]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 67486135(S)-N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 68482615(s)-1-(5-(3-(2-Methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

In 1 L of absolute ethanol was added (S)—N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-amine (41 g, 76.7 mmol) and the reaction was heated to 80° C. 41 mL of aqueous HCl (11.6 mL of concentrated HCl diluted in water) was added. After 2 hours, the resultant solid material was hot filtered, washed with ethanol (200 mL) and dried in vacuo to yield crude product as a solid which contained about 2% starting material. The solids were suspended in EtOH (1 L) and heated to 80° C. followed by 41 mL of aqueous HCl (11.6 mL of concentrated HCl diluted in water). After 3.5 hours the resultant solid material was hot filtered, washed with ethanol (200 mL) and dried in vacuo and to afford (S)-1-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol hydrochloride (35 g, 85%). Mass Spectrum (apci) m/z=455.2 (M+H−HCl).

Workup

  1. washwashed with ethanol (200 mL)
  2. customdried in vacuo
  3. customto yield crude product as a solid which
  4. temperatureheated to 80° C.
  5. waitAfter 3.5 hours the resultant solid material was hot
  6. washfiltered, washed with ethanol (200 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a474236482214c64a3a4a3324c6ca389
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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