Hydrochloric Acid → 1-Cyclopropyl-2-(5-methyl-1,3,4-oxadiazol-2-yl)propan-2-amine

HRID 1480243Notes

Reaction equation

HRID 1480243 reaction equation
[CH:1]1([CH2:4][C:5]([NH:13]S(C(C)(C)C)=O)([CH3:12])[C:6]2[O:7][C:8]([CH3:11])=[N:9][N:10]=2)[CH2:3][CH2:2]1.Cl.O1CCOCC1>CO>[CH:1]1([CH2:4][C:5]([C:6]2[O:7][C:8]([CH3:11])=[N:9][N:10]=2)([NH2:13])[CH3:12])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90203435HCID 90203435, compound

Product 1

HCID 902046221-Cyclopropyl-2-(5-methyl-1,3,4-oxadiazol-2-yl)propan-2-amineYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[2-cyclopropyl-1-methyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]-2-methyl-propane-2-sulfinamide (example 173a, 520 mg, 1.46 mmol) in MeOH (8 ml) was added a 4M solution of hydrochloric acid in dioxane (729 μl, 2.92 mmol). The reaction mixture was stirred at room temperature for 1 hour. Reaction was quenched by addition of potassium carbonate and stirred for 15 minutes. The insolubles were removed by filtration and the filtrate was evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane-methanol gradient to yield the title compound (130 mg, 50%). MS (ESI, m/z): 182.2 (M+H+).

Workup

  1. customReaction
  2. customwas quenched by addition of potassium carbonate
  3. stirringstirred for 15 minutes
  4. customThe insolubles were removed by filtration
  5. customthe filtrate was evaporated down to dryness
  6. customThe crude material was purified by flash chromatography on silica eluting with a dichloromethane-methanol gradient

Sources & evidence

ORD record
ord-42c909ab5fa149e1a28074b79c90a81c
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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