Hydrochloric Acid → 3-(1,3-Thiazol-2-yl)oxetan-3-amine hydrochloride

HRID 927725

Reaction equation

HRID 927725 reaction equation
[ClH:1].[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1([NH:11]S(C(C)(C)C)=O)[CH2:10][O:9][CH2:8]1>O1CCOCC1.CO>[ClH:1].[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1([NH2:11])[CH2:10][O:9][CH2:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 711130582-Methyl-propane-2-sulfinic acid (3-thiazol-2-yl-oxetan-3-yl)-amide

Product 1

HCID 866747823-(1,3-Thiazol-2-yl)oxetan-3-amine hydrochlorideYield 70.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A 4.0 M solution of hydrochloric acid (117 μL, 467 μmol) in dioxane was added to a solution of 2-methyl-propane-2-sulfinic acid (3-thiazol-2-yl-oxetan-3-yl)-amide (Example 281a) (81 mg, 311 μmol) in methanol (0.5 mL) at 0° C. The mixture was stirred at 0° C. for 5 min before the solvents were removed under reduced pressure. The resulting white solid was triturated with diethyl ether and filtered off. The solid was further washed with diethyl ether and dried under high vacuum to yield the title compound (42 mg, 70%) as a white solid. MS (EI): m/e=157.1 [M+H]+.

Workup

  1. customwere removed under reduced pressure
  2. customThe resulting white solid was triturated with diethyl ether
  3. filtrationfiltered off
  4. washThe solid was further washed with diethyl ether
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-fdcf8c05978b4890bf53b9e11c3c7c63
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Linked notes

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