Hydrochloric Acid → HCID 68484058, compound

HRID 534132Notes

Reaction equation

HRID 534132 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@@:28]4([CH3:35])[CH2:32][O:31]C(C)(C)[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:36]>CCO>[ClH:36].[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@@:28]([OH:29])([CH3:35])[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 Acid3×HCID 68478040HCID 68478040, compound

Product 1

HCID 68484058HCID 68484058, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-3-(2,2,4-trimethyl-1,3-dioxolane-4-yl)-1,2,4-thiadiazol-5-amine (55 mg, 0.108 mmol) was dissolved in EtOH (3 mL). 1M HCl (0.3 mL) was added and the mixture was stirred at ambient temperature for 24 hours. Additional 1M HCl (0.3 mL) was added and the mixture was stirred overnight. The mixture was partitioned between saturated aqueous sodium bicarbonate and CH2Cl2, dried over sodium sulfate, filtered and concentrated. The residue was purified over silica gel (15% methanol in EtOAc) to afford (S)-2-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)propane-1,2-diol hydrochloride (34.9 mg, 0.0691 mmol, 63.9% yield) as a white solid after HCl salt formation. Mass Spectrum (apci) m/z=451.1 (M+H−H2O−HCl) (100) and 469.1 (M+H−HCl) (30).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe mixture was partitioned between saturated aqueous sodium bicarbonate and CH2Cl2
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified over silica gel (15% methanol in EtOAc)

Sources & evidence

ORD record
ord-f2ef5e1844684e398d7d5d1ab564035c
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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