3,4-difluoro-2-[2-fluoro-4-(3-hydroxy-3-methyl-1-pentynyl)anilino]-N-(2-hydroxyethoxy)benzamide → 3,4-difluoro-2-[2-fluoro-4-(3-hydroxy-3-methylpentyl)anilino]-N-(2-hydroxyethoxy)benzamide
Reaction equation
[F:1][C:2]1[C:3]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[C:24][C:25]([OH:29])([CH3:28])[CH2:26][CH3:27])=[CH:19][C:18]=2[F:30])=[C:4]([CH:12]=[CH:13][C:14]=1[F:15])[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6]>C(O)C.[Pd]>[F:1][C:2]1[C:3]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([OH:29])([CH3:28])[CH2:26][CH3:27])=[CH:19][C:18]=2[F:30])=[C:4]([CH:12]=[CH:13][C:14]=1[F:15])[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The product of Example 13, 3,4-difluoro-2-[2-fluoro-4-(3-hydroxy-3-methyl-1-pentynyl)anilino]-N-(2-hydroxyethoxy)benzamide was hydrogenated in absolute ethanol in the presence of 5% Pd/C by the general procedure of Example 1, Step D. The resulting crude solid was purified by filtration through a plug of silica (MeOH as eluant) to give 3,4-difluoro-2-[2-fluoro-4-(3-hydroxy-3-methylpentyl)anilino]-N-(2-hydroxyethoxy)benzamide (98%) as a light yellow foam (hygroscopic). 1H NMR [400 MHz, (CD3)2SO] δ 9.62 (br s, 1 H), 7.54–7.48 (m, 1 H), 7.04–6.96 (m, 2 H), 6.86 (dd, J=8.2, 1.6 Hz, 1 H), 6.75 (ddd, J=8.6, 5.2 Hz, 1 H), 4.08 (br s, 1 H), 3.80 (t, J=4.9 Hz, 2 H), 3.53 (t, J=4.9 Hz, 2 H), 2.55–2.50 (m, 2 H), 1.60–1.54 (m, 2 H), 1.41 (q, I=7.6 Hz, 2 H), 1.06 (s, 3 H), 0.84 (t, J=7.6 Hz, 3 H). HRMS (EI+) calcd for C21H25F3N2O4 426.1766 (M+), found 426.1770.
Workup
- filtrationThe resulting crude solid was purified by filtration through a plug of silica (MeOH as eluant)
Sources & evidence
- ORD record
- ord-4595e47307364b58b48b58bd2015dbac
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07078438B2
Reaction notes
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