HCID 10089688, compound → HCID 22475622, compound

HRID 2184092Notes

Reaction equation

HRID 2184092 reaction equation
[F:1][C:2]([F:28])([F:27])[CH2:3][N:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)[CH2:5][C:6](=[O:10])[CH2:7][CH2:8][CH3:9].CN(C1C=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=1)CC(=[O:36])CCC>>[OH2:10].[C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:36].[F:1][C:2]([F:27])([F:28])[CH2:3][N:4]([C:11]1[CH:12]=[CH:13][C:14]([C:17]([OH:26])([C:22]([F:23])([F:24])[F:25])[C:18]([F:21])([F:19])[F:20])=[CH:15][CH:16]=1)[CH2:5][CH:6]([OH:10])[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 10089688HCID 10089688, compoundHCID 22475623HCID 22475623, compound

Product 2

HCID 22392675Trifluoroacetic acid waterHCID 22475622HCID 22475622, compoundYield 71%

Procedure

Prepared in the manner of Example 34 except 1-((2,2,2-trifluoroethyl){4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}amino)pentan-2-one was substituted for 1-(methyl{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-phenyl}amino)-pentan-2-one. Purification by reverse phase HPLC using a gradient elution of 80:20 H2O/TFA:CH3CN to 50:50 H2O/TFA:CH3CN at 254 nm afforded the title compound as white solid (71%). 1H NMR (CDCl3) δ 7.48 (d, 2H), 6.77 (d, 2H), 4.05 (q, 2H), 3.98 (m, 1H), 3.53 (dd, 1H), 3.13 (dd, 1H), 1.42 (m, 4H), 0.91 (t, 3H). Anal. Calc. for C16H18NO2F9: C, 44.97; H, 4.25; N, 3.28. Found: C, 44.77; H, 4.49; N, 3.19. HRMS (MH+). Calc.: 428.1272. Found: 428.1289.

Workup

  1. customPurification by reverse phase HPLC
  2. washa gradient elution of 80:20 H2O/TFA

Sources & evidence

ORD record
ord-f54009c280674a3591f1553500dd9ff3
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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