Trifluoroacetic acid → HCID 118045746, compound

HRID 595884Notes

Reaction equation

HRID 595884 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][C:7]1[N:8]=[CH:9][C:10]([NH:13]C(=O)OC(C)(C)C)=[N:11][CH:12]=1)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][S:2]([CH2:5][CH2:6][C:7]1[N:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118046348HCID 118046348, compound

Product 1

HCID 118045746HCID 118045746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 5-(2-(methylsulfonyl)ethyl)pyrazin-2-ylcarbamate (320 mg, 1.062 mmol) in DCM (6 mL) was added TFA (2.5 mL, 32.4 mmol) and stirred at room temperature for 1 hour. The solvent was concentrated off to constant mass. The product was free based by using solid supported carbonate 2.5 grams at 0.8 mmol/gram with 6 mL of acetonitrile and stirred for 5 min. The solid support was filtered off and flush with acetonitrile. The product was concentrated to constant mass to give the desired product used as is, assume quantitative yield (1.062 mmol). LCMS (m/z): 202.1 (MH+), 0.20 min.

Workup

  1. concentrationThe solvent was concentrated off to constant mass
  2. stirringstirred for 5 min
  3. filtrationThe solid support was filtered off
  4. customflush with acetonitrile
  5. concentrationThe product was concentrated to constant mass

Sources & evidence

ORD record
ord-e459c506e81c4f8ead9c90140dbc434e
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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