tert-Butyl 4-(4-((2-(6-(4-(ethoxycarbonyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-4-methylphenoxy)methyl)phenyl)-3,6-dihydropyridine-1 (2H)-carboxylate → tert-Butyl 4-(4-((2-(6-(4-(ethoxycarbonyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-4-methylphenoxy)methyl)phenyl)piperidine-1-carboxylate

HRID 1891224Notes

Reaction equation

HRID 1891224 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[N:20]=[C:19]([C:21]3[CH:47]=[C:46]([CH3:48])[CH:45]=[CH:44][C:22]=3[O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH2:32][CH2:33][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:35][CH:36]=4)=[CH:27][CH:26]=3)[CH:18]=[CH:17][CH:16]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2].[H][H]>CCOC(C)=O.[Pt](=O)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[N:20]=[C:19]([C:21]3[CH:47]=[C:46]([CH3:48])[CH:45]=[CH:44][C:22]=3[O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([CH:31]4[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:42])([CH3:43])[CH3:41])=[O:38])[CH2:33][CH2:32]4)=[CH:27][CH:26]=3)[CH:18]=[CH:17][CH:16]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 86644574tert-Butyl 4-(4-((2-(6-(4-(ethoxycarbonyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-4-methylphenoxy)methyl)phenyl)-3,6-dihydropyridine-1 (2H)-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86644575tert-Butyl 4-(4-((2-(6-(4-(ethoxycarbonyl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)-4-methylphenoxy)methyl)phenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a degassed solution of the title compound from Example 12 Step D (365 mg, 0.551 mmol) in EtOAc (10 mL) was added platinum(IV) oxide (125 mg). The reaction flask was fitted with a hydrogen balloon attached to a 3-way adapter. The reaction mixture was then evacuated and back-filled with hydrogen. After this process was repeated three times, the reaction mixture was placed under a hydrogen atmosphere, and was stirred vigorously. After 40 min, the reaction mixture was filtered though Celite, rinsing with EtOAc. Purification by flash chromatography on silica gel (0 to 50% EtOAc in hexanes, then 50 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 665.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.16 (d, J=8.0 Hz, 1 H), 8.12 (s, 1H), 7.86 (t, J=8.0 Hz, 1H), 7.79 (br s, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.30 (d, J=8.0 Hz, 2H), 7.19-7.16 (m, 3H), 6.97 (d, J=8.5 Hz, 1H), 5.09 (s, 2H), 4.38 (q, J=7.0 Hz, 2H), 4.30-4.18 (m, 2H), 2.82-2.78 (m, 2H), 2.67-2.62 (m, 1H), 2.35 (s, 3H), 1.83-1.80 (m, 2H), 1.66-1.57 (m, 2H), 1.49 (s, 9H), 1.40 (t, J=7.0 Hz, 3H).

Workup

  1. customattached to a 3-way adapter
  2. customThe reaction mixture was then evacuated
  3. additionback-filled with hydrogen
  4. filtrationthe reaction mixture was filtered though Celite
  5. washrinsing with EtOAc
  6. customPurification by flash chromatography on silica gel (0 to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-2ea024a65da64ed182c084d3be722f54
Source dataset
uspto-grants-2013_08
Patent number
US08507512B2

Reaction notes

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