Methyl (2E)-4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpent-2-enoate → Methyl 4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpentanoate
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH:14][C:15]([CH3:23])([CH3:22])/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])[S:12][CH:13]=2)=[CH:5][CH:4]=1)#[N:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([NH:14][C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[S:12][CH:13]=2)=[CH:7][CH:8]=1)#[N:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl (2E)-4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpent-2-enoate (0.85 g, 2.6 mmol), prepared in step 1 of Example 87, was dissolved in ethyl acetate (10 mL) and 10% Pd on carbon (0.25 g, 0.20 mmol) was added. The mixture was shaken in a Parr apparatus under 40 psi of hydrogen for 16 h. The mixture was diluted with ethyl acetate, filtered through the Celite™ reagent and concentrated. Flash chromatography (10% acetone/hexane) afforded methyl 4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpentanoate (0.81 g, 95%) as a white solid. HRMS: calcd for C17H19N3O2S+H+, 330.12707; found (ESI, [M+H]+), 330.1292; Analytical HPLC: purity 100% at 210-370 nm, 11.2 min; 100% at 272 nm, 11.2 min; the Xterra® RP18 column, 3.5%, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.
Workup
- filtrationfiltered through the Celite™ reagent
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-08f3e7fbac8d4133bef8f8dcc7e19604
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07618990B2
Reaction notes
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