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

HRID 534035
Notes
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Reaction equation

HRID 534035 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:8]=[C:9]([O:29][C:30]2[C:31]([CH3:36])=[N:32][CH:33]=[CH:34][CH:35]=2)[C:10]([NH:13][C:14]2[S:18][N:17]=[C:16]([C@H:19]3[CH2:23][O:22]C4(CCCCC4)[O:20]3)[N:15]=2)=[N:11][CH:12]=1.[ClH:37].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(OCC)(=O)C>[ClH:37].[CH3:1][O:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:8]=[C:9]([O:29][C:30]2[C:31]([CH3:36])=[N:32][CH:33]=[CH:34][CH:35]=2)[C:10]([NH:13][C:14]2[S:18][N:17]=[C:16]([C@H:19]([OH:20])[CH2:23][OH:22])[N:15]=2)=[N:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 68481884(S)-N-(5-(3-methoxypropylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decan-2-yl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 67487758(S)-1-(5-(5-(3-methoxypropylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol hydrochlorideYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

(S)-N-(5-(3-methoxypropylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decane-2-yl)-1,2,4-thiadiazol-5-amine (85 mg, 0.16 mmol) was dissolved in ethanol (5 ml) and 1M HCl (0.5 ml) was added. The mixture was heated to 70° C. and agitated 3 hours. Upon cooling, the reaction was diluted with ethyl acetate, basified with sodium carbonate solution and washed with water and brine, dried (MgSO4), filtered and evaporated. The resulting solid was dissolved in small amount of dichloromethane and treated with 1M HCl in ether. After evaporation, (S)-1-(5-(5-(3-methoxypropylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)ethane-1,2-diol hydrochloride (65 mg, 90% yield) was obtained as white solid. Mass Spectrum (apci) m/z=450.1 (M+H−HCl).

Workup

  1. temperatureUpon cooling
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe resulting solid was dissolved in small amount of dichloromethane
  7. additiontreated with 1M HCl in ether
  8. customAfter evaporation

Sources & evidence

ORD record
ord-6ef50f031da14523a0e8fec705b674aa
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853409B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes