HCID 10089688, compound → HCID 10410704, compound

HRID 2184091Notes

Reaction equation

HRID 2184091 reaction equation
[CH2:1]([N:8]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:9][C:10](=[O:14])[CH2:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C1C=CC(C(O)(C(F)(F)F)C(F)(F)F)=CC=1)CC(=[O:38])CCC>>[OH2:14].[C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:38].[CH2:1]([N:8]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:23])[F:24])=[CH:17][CH:16]=1)[CH2:9][CH:10]([OH:14])[CH2:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10089688HCID 10089688, compoundHCID 22475626HCID 22475626, compound

Product 2

HCID 10410704HCID 10410704, compoundHCID 22392675Trifluoroacetic acid water

Procedure

Prepared in the manner of Example 34 except 1-(benzyl{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 60:40 H2O/TFA:CH3CN to 0:100 H2O/TFA:CH3CN at 254 nm afforded the title compound as an yellow waxy solid (34%). 1H NMR (CDCl3) δ 7.48 (d, 2H), 7.33 (t, 2H), 7.27 (m, 1H), 7.20 (d, 2H), 6.81 (d, 2H), 4.70 (s, 2H), 4.03 (m, 1H), 3.56 (dd, 1H), 3.41 (dd, 1H), 1.50 (m, 4H), 0.97 (t, 3H). Anal. Calc. for C21H23NO2F6+0.1 TFA+0.5 H2O: C, 55.64; H, 5.35; N, 3.06. Found: C, 55.71; H, 5.56; N, 2.73. HRMS (MH+). Calc.: 436.1711. Found: 436.1728.

Workup

  1. customPurification by reverse phase HPLC
  2. washa gradient elution of 60:40 H2O/TFA

Sources & evidence

ORD record
ord-72b428d79d1c490ab65673425d23e9b1
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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