Trifluoroacetic acid → 1-(4-(5-(6-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)isoxazol-3-yl)phenyl)-N-methylmethanamine

HRID 522534Notes

Reaction equation

HRID 522534 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:25]=[C:24]([C:26]3[O:30][N:29]=[C:28]([C:31]4[CH:36]=[CH:35][C:34]([CH2:37][N:38](C)[C:39](=O)OC(C)(C)C)=[CH:33][CH:32]=4)[CH:27]=3)[CH:23]=[N:22][CH:21]=2)=[CH:16][CH:15]=1)(=[O:13])=[O:12])([CH3:10])[CH3:9]>C(Cl)Cl>[CH:8]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:25]=[C:24]([C:26]3[O:30][N:29]=[C:28]([C:31]4[CH:32]=[CH:33][C:34]([CH2:37][NH:38][CH3:39])=[CH:35][CH:36]=4)[CH:27]=3)[CH:23]=[N:22][CH:21]=2)=[CH:18][CH:19]=1)(=[O:12])=[O:13])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67480464tert-butyl N-[[4-[5-[6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]isoxazol-3-yl]phenyl]methyl]-N-methyl-carbamate

Product 1

HCID 534951701-(4-(5-(6-(4-(isopropylsulfonyl)phenyl)pyrazin-2-yl)isoxazol-3-yl)phenyl)-N-methylmethanamineYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (500 μL, 6.490 mmol) was added to a stirred solution of tert-butyl N-[[4-[5-[6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]isoxazol-3-yl]phenyl]methyl]-N-methyl-carbamate (85 mg, 0.1549 mmol) in DCM (5 mL) and the reaction was stirred at ambient temperature for 15 hours. The solvent was removed in vacuo and the residue azeotroped with DCM (×2) and ether (×2). The reaction mixture was passed through a 2 g SCX-2 cartridge and washed with MeOH/DCM mixtures. The product was eluted by washing the cartridge with 2M NH3 in MeOH/DCM mixtures. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (45.6 mg, 66% Yield). 1H NMR (400.0 MHz, DMSO) d H NMR (400.0 MHz, DMSO) δ 9.67 (s, 1H), 9.46 (s, 1H), 8.72 (d, 2H), 8.21 (d, 2H), 8.19 (s, 1H), 8.11 (d, 2H), 7.67 (d, 2H), 3.87 (s, 2H), 3.69 (sept, 1H), 2.43 (s, 3H) and 1.35 (d, 6H) ppm; MS (ES+) 449.2; LCMS Retention time: 1.09 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with DCM (×2) and ether (×2)
  3. washwashed with MeOH/DCM
  4. washThe product was eluted
  5. washby washing the cartridge with 2M NH3 in MeOH/DCM mixtures
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d68778d475e54e3289f3f5b88c10be01
Source dataset
uspto-grants-2016_05
Patent number
US09334244B2

Reaction notes

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