Methanesulfonic Acid → HCID 58466174, compound

HRID 335750Notes

Reaction equation

HRID 335750 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([C:27]#[C:28][C:29]([CH3:32])([OH:31])[CH3:30])=[CH:10][CH:11]=3)[N:6]=1.[CH3:33]S(O)(=O)=O.C(=O)(O)[O-].[Na+]>CO>[CH3:33][O:31][C:29]([CH3:32])([CH3:30])[C:28]#[C:27][C:9]1[CH:8]=[C:7]2[C@@:5]3([CH2:4][O:3][C:2]([NH2:1])=[N:6]3)[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)[CH:18]=3)[O:13][C:12]2=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 67241904HCID 67241904, compound

Product 1

HCID 58466174HCID 58466174, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A vial was charged with (S)-4-(2′-amino-3-p-tolyl-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl)-2-methylbut-3-yn-2-ol (134.5 mg, 0.316 mmol), MeOH (3161 μL), and methanesulfonic acid (103 μL, 1.581 mmol). The vial was sealed and placed in a 70° C. oil bath for 4 hours. The mixture was poured into saturated aq. sodium bicarbonate solution (30 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was chromatographed on a 40-g Redi-Sep column to give a impure material that was dissolved in methanol and purified by reverse-phase HPLC (10-90% CH3CN/H2O with 0.1% TFA). The fractions containing product were combined in saturated aq. sodium bicarbonate solution with the aid of methanol, and the mixture was extracted with DCM (3×). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated to give (S)-7-(3-methoxy-3-methylbut-1-ynyl)-3-p-tolyl-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine.

Workup

  1. customThe vial was sealed
  2. customplaced in a 70° C.
  3. customfor 4 hours
  4. extractionextracted with EtOAc (2×25 mL)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed on a 40-g Redi-Sep column
  9. customto give a impure material that
  10. custompurified by reverse-phase HPLC (10-90% CH3CN/H2O with 0.1% TFA)
  11. additionThe fractions containing product
  12. extractionthe mixture was extracted with DCM (3×)
  13. dry with materialThe combined organic extracts were dried over sodium sulfate
  14. filtrationfiltered
  15. customevaporated

Sources & evidence

ORD record
ord-9a3adde10cea4d6182ed99b0ab9f345a
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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