Hydrochloric Acid → HCID 68479286, compound

HRID 1523623Notes

Reaction equation

HRID 1523623 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[C:32]([CH3:34])([CH3:33])[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:37]>CCO>[ClH:37].[CH3:34][C:32]([OH:31])([CH3:33])[C@H:28]([C:25]1[N:24]=[C:23]([NH:22][C:10]2[C:9]([O:8][C:7]3[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=3)=[CH:14][C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:12][N:11]=2)[S:27][N:26]=1)[OH:29]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 67486618HCID 67486618, compound

Product 1

HCID 68479286HCID 68479286, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)—N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)-1,2,4-thiadiazol-5-amine (145 mg, 0.2774 mmol) was dissolved in EtOH (5 mL), and 6M HCl (0.3 mL) was added. The reaction was stirred at ambient temperature for 2 hours and then at 70° C. for 2 hours. The reaction was cooled to ambient temperature and partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate. The organic layer was dried, filtered, concentrated and purified over silica gel (10% methanol in EtOAc) to afford (S)-2-methyl-1-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)propane-1,2-diol hydrochloride (111.7 mg, 0.215 mmol, 77.6% yield) as a pale yellow solid after HCl salt formation. Mass Spectrum (apci) m/z=465.2 (M+H−HCl).

Workup

  1. waitat 70° C. for 2 hours
  2. temperatureThe reaction was cooled to ambient temperature
  3. custompartitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified over silica gel (10% methanol in EtOAc)

Sources & evidence

ORD record
ord-9a1afd88f52949fd83c6f38d79949ed1
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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