2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 67385800, compound

HRID 906027Notes

Reaction equation

HRID 906027 reaction equation
CCN(C(C)C)C(C)C.Cl.Cl.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[CH2:18][NH:19][C:20]([NH:22][C:23]1[N:24]=[C:25]2[CH:31]=[CH:30][N:29]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:26]2=[N:27][CH:28]=1)=[O:21].O([CH2:48][C:49]([F:52])([F:51])[F:50])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[F:50][C:49]([F:52])([F:51])[CH2:48][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[CH2:18][NH:19][C:20]([NH:22][C:23]1[N:24]=[C:25]2[CH:31]=[CH:30][N:29]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:26]2=[N:27][CH:28]=1)=[O:21]

Participants

5

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 81531DiisopropylethylamineHCID 67385466HCID 67385466, compound

Product 1

HCID 67385800HCID 67385800, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (0.13 mL, 0.732 mmol) was added at 0° C. to a suspension of 1-piperidin-2-ylmethyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea dihydrochloride (0.080 g, 0.198 mmol) in 10 mL of DCM. The resulting mixture was stirred at RT for 15 minutes before adding 2,2,2-trifluoroethyl triflate (0.056 mL, 0.396 mmol) was added. The reaction mixture was stirred at RT overnight before being evaporated. The residue was purified by SiO2 flash chromatography to give 0.053 mg of racemic 1-[1-(2,2,2-trifluoro-ethyl)-piperidin-2-ylmethyl]-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (55% yield).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at RT overnight
  3. custombefore being evaporated
  4. customThe residue was purified by SiO2 flash chromatography

Sources & evidence

ORD record
ord-ff55f8f8b83145e0a38a07a8bf84ec68
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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