Trifluoroacetic acid → 3-Ethynyl-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

HRID 68656Notes

Reaction equation

HRID 68656 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]([C:23]1[C:28]([C:29]#[CH:30])=[N:27][C:26]([C:31]2[CH:36]=[CH:35][C:34]([S:37]([CH:40]([CH3:42])[CH3:41])(=[O:39])=[O:38])=[CH:33][CH:32]=2)=[CH:25][N:24]=1)C(=O)OC(C)(C)C)=O)(C)(C)C>C(Cl)Cl>[C:29]([C:28]1[C:23]([NH2:15])=[N:24][CH:25]=[C:26]([C:31]2[CH:32]=[CH:33][C:34]([S:37]([CH:40]([CH3:41])[CH3:42])(=[O:39])=[O:38])=[CH:35][CH:36]=2)[N:27]=1)#[CH:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59471983N,N-Di(Boc)-3-ethynyl-5-[4-(isopropylsulfonyl)phenyl]pyrazin-2-amine

Product 1

HCID 546706613-Ethynyl-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amineYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (34.45 g, 23.28 mL, 302.1 mmol) was added to a stirred solution of tert-butyl N-tert-butoxycarbonyl-N-[3-ethynyl-5-(4-isopropylsulfonylphenyl)pyrazin-2-yl]carbamate (5 g, 9.968 mmol) in DCM (200 mL) and the reaction mixture stirred at ambient temperature for 1.5 hours. The solvent was removed in vacuo and the residue re-dissolved in DCM and stirred with saturated aqueous NaHCO3 for 30 minutes. The layers were separated and the organic layer washed with saturated aqueous NaHCO3 (×3). The combined aqueous layers were extracted with DCM (×3) and the combined organic extracts dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated from DCM and precipitate isolated by filtration and dried under vacuum to give the title product as a beige solid (2.8 g, 93% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.18 (d, 6H), 3.44 (t, 1H), 4.76 (s, 1H), 7.01 (s, 2H), 7.89 (d, 2H), 8.20 (d, 2H) and 8.75 (s, 1H) ppm; MS (ES+) 302.12.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue re-dissolved in DCM
  3. stirringstirred with saturated aqueous NaHCO3 for 30 minutes
  4. customThe layers were separated
  5. washthe organic layer washed with saturated aqueous NaHCO3 (×3)
  6. extractionThe combined aqueous layers were extracted with DCM (×3)
  7. dry with materialthe combined organic extracts dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated from DCM
  11. customprecipitate
  12. customisolated by filtration
  13. customdried under vacuum

Sources & evidence

ORD record
ord-2d915828f5394521983e962f63c547aa
Source dataset
uspto-grants-2014_09
Patent number
US08822469B2

Reaction notes

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