Trifluoroacetic acid → HCID 88085277, compound

HRID 497430Notes

Reaction equation

HRID 497430 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=C)[N:15]([C:18]4[CH:23]=[CH:22][C:21]([N:24]5[CH:28]=[CH:27][N:26]=[C:25]5[CH2:29][N:30]([CH3:41])C(=O)OCC5C=CC=CC=5)=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:43]([F:46])([F:45])[F:44])=[N:10]2)=[CH:5][CH:4]=1.[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48]>>[F:50][C:49]([F:52])([F:51])[C:47]([OH:53])=[O:48].[F:50][C:49]([F:52])([F:51])[C:47]([OH:53])=[O:48].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]3[C:14](=[O:48])[N:15]([C:18]4[CH:19]=[CH:20][C:21]([N:24]5[CH:28]=[CH:27][N:26]=[C:25]5[CH2:29][NH:30][CH3:41])=[CH:22][CH:23]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:43]([F:46])([F:45])[F:44])=[N:10]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86759850HCID 86759850, compound

Product 1

HCID 88085277HCID 88085277, compound

Procedure

Benzyl (1-{4-[1-(4-methoxyphenyl)-7-methylene-3-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]phenyl}-1H-imidazol-2-yl)methyl(methyl)carbamate (100 mg) was heated with 5 mL of TFA at 80° C. for 1 h. The solvent was removed and dried under vacuum. The crude product was purified by reverse phase HPLC (C18 reverse phase column, eluted with a H2O/CH3CN gradient with 0.05% TFA) to give 20.0 mg of the desired product as the bis-TFA salt. MS (ES+): 497.5, (M+H)+. 1HNMR (CDCl3): δ 7.53-7.39 (m, 6H), 7.27 (s, 1H), 7.20 (s, 1H), 6.95 (d, 2H), 4.25 (s, 2H), 4.23 (t, 2H), 3.84 (s, 3H), 3.22 (t, 2H), 2.74 (s, 3H).

Workup

  1. customThe solvent was removed
  2. customdried under vacuum
  3. customThe crude product was purified by reverse phase HPLC (C18 reverse phase column
  4. washeluted with a H2O/CH3CN gradient with 0.05% TFA)

Sources & evidence

ORD record
ord-d0587fb170f14f80be1514b7b04e20fd
Source dataset
uspto-grants-2005_09
Patent number
US06949550B2

Reaction notes

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