HCID 23571150, compound → HCID 23571151, compound

HRID 1180628Notes

Reaction equation

HRID 1180628 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[S:15][C:14]([C:16]3[CH:17]=[CH:18][C:19]4[CH2:26][CH:25]5[C:27]6([CH2:31][N:30]([CH2:32][C:33]([F:36])([F:35])[F:34])[S:29](=[O:38])(=[O:37])[NH:28]6)[CH:22]([CH2:23][CH2:24]5)[CH2:21][C:20]=4[CH:39]=3)=[N:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[H][H]>[Pd].C(OCC)(=O)C>[F:41][C:2]([F:1])([F:40])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[S:15][C:14]([C:16]3[CH:17]=[CH:18][C:19]4[CH2:26][CH:25]5[C:27]6([CH2:31][N:30]([CH2:32][C:33]([F:36])([F:35])[F:34])[S:29](=[O:37])(=[O:38])[NH:28]6)[CH:22]([CH2:23][CH2:24]5)[CH2:21][C:20]=4[CH:39]=3)=[N:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 23571150HCID 23571150, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23571151HCID 23571151, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the tetrahydropyridine from Example 41 (0.018 g, 0.029 mmol), palladium on carbon (0.01 g) and ethyl acetate (2 mL) was stirred under 1 atmosphere of hydrogen for 16 hours. The catalyst was removed by filtration through a glass fibre pad and the solvent removed in vacuo to give the title compound (0.018 g, quant.). δ (1H, 400 MHz, CDCl3) 1.29-1.38 (2H, m), 1.68-1.82 (4H, m), 2.16-2.20 (2H, m), 2.46-2.49 (2H, m), 2.70-2.80 (2H, m), 2.92-2.98 (1H, m), 3.18-3.33 (4H, m), 3.44 (2H, s), 3.64-3.72 (2H, m), 4.11-4.15 (1H, m), 4.64 (1H, d, J=14 Hz), 4.91 (1H, s) 7.15 (1H, d, J=7.8 Hz), 7.55 (1H, d, J=0.7 Hz), 7.61 (1H, dd, J=1.5 & 7.8 Hz), 7.66 (1H, s). MS (ES+) 623 ([MH]+).

Workup

  1. customThe catalyst was removed by filtration through a glass fibre pad
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ed2c1661c0db41f98e59ad1651b65c0f
Source dataset
uspto-grants-2007_10
Patent number
US07282513B2

Reaction notes

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