Trifluoroacetic acid → HCID 72706748, compound

HRID 595265Notes

Reaction equation

HRID 595265 reaction equation
C(O)(C(F)(F)F)=O.[Si]([O:15][CH2:16][CH2:17][N:18]1[CH:22]=[C:21]([C:23]2[CH:24]=[C:25]([NH:30][C:31]3[N:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][N:32]=3)[CH:26]=[C:27]([CH3:29])[CH:28]=2)[CH:20]=[N:19]1)(C(C)(C)C)(C)C>ClCCl>[CH3:29][C:27]1[CH:28]=[C:23]([C:21]2[CH:20]=[N:19][N:18]([CH2:17][CH2:16][OH:15])[CH:22]=2)[CH:24]=[C:25]([NH:30][C:31]2[N:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:33][N:32]=2)[CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131734580HCID 131734580, compound

Product 1

HCID 72706748HCID 72706748, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (24 μL, 0.31 mmol) was added to a solution of N-{3-[1-(2-{[tert-butyl(dimethyl)silyl]-oxy}ethyl)-1H-pyrazol-4-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine in dichloromethane (2 mL), and the reaction was allowed to stir for 30 minutes. The competed reaction was concentrated under reduced pressure. The residue was purified by reverse phase HPLC (ACN/water with 0.1% formic acid modifier to afford 2-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]ethanol. MS ESI calcd. for C17H17F3N5O [M+H]+ 364. found 364. 1H NMR (500 MHz, DMSO-d6) δ 10.10 (s, 1H), 8.79 (d, J=4.9, 1H), 8.00 (s, 1H), 7.81 (s, 1H), 7.73 (s, 1H), 7.31 (s, 1H), 7.23 (d, J=4.9, 1H), 7.05 (s, 1H), 4.92 (t, J=5.2, 1H), 4.14 (t, J=5.6, 2H), 3.73 (q, J=5.6, 2H), 2.27 (s, 3H).

Workup

  1. customThe competed reaction
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was purified by reverse phase HPLC (ACN/water with 0.1% formic acid modifier

Sources & evidence

ORD record
ord-7343f29416a44645af111a9ac1817964
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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