Trifluoroacetic acid → N-(3-(aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide

HRID 1887684Notes

Reaction equation

HRID 1887684 reaction equation
[CH3:1][N:2]([C:7]1[C:12]([CH2:13][NH:14]C(=O)OC(C)(C)C)=[CH:11][CH:10]=[CH:9][N:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:14][CH2:13][C:12]1[C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4])=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58155014tert-butyl (2-(N-methylmethylsulfonamido)pyridin-3-yl)methylcarbamate

Product 1

HCID 45480403N-(3-(aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 mL round bottom flask charged with tert-butyl (2-(N-methylmethylsulfonamido)pyridin-3-yl)methylcarbamate (118 mg, 0.26 mmol) was added a 40% solution of TFA in CH2Cl2 (4 mL). The resulting mixture was stirred for 20 min, then the volatiles were evaporated. Toluene (4 mL) was added to the crude followed by evaporation. This procedure was repeated once. A solution of the crude residue in CH2Cl2 (4 mL) was treated with Amberlyst A-21 (1.8 g) and stirred for 30 min. The Amberlyst A-21 resin was filtered off and washed with CH2Cl2 (20 mL). The volatiles were evaporated to yield N-(3-(aminomethyl)pyridin-2-yl)-N-methylmethanesulfonamide (50 mg, 0.23 mmol, 88%).

Workup

  1. customthe volatiles were evaporated
  2. additionToluene (4 mL) was added to the crude
  3. customfollowed by evaporation
  4. additionA solution of the crude residue in CH2Cl2 (4 mL) was treated with Amberlyst A-21 (1.8 g)
  5. stirringstirred for 30 min
  6. filtrationThe Amberlyst A-21 resin was filtered off
  7. washwashed with CH2Cl2 (20 mL)
  8. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-951da8c396884dfba254800298464a49
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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