HCID 86687972, compound → HCID 86687971, compound

HRID 2370795Notes

Reaction equation

HRID 2370795 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:23]2[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:26]=[CH:25][N:24]=2)[NH:10][C:11]([C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][CH:19]=[N:20]3)=[CH:15][CH:14]=2)=[O:12])=[CH:5][CH:4]=1>CO.[OH-].[Pd+2].[OH-].[Pd]>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:23]2[C:28]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:26]=[CH:25][N:24]=2)[NH:10][C:11]([C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][CH2:19][NH:20]3)=[CH:15][CH:14]=2)=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 86687972HCID 86687972, compound

Product 1

HCID 86687971HCID 86687971, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)—N-((4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)-pyridin-2-yl)methyl)quinoline-7-carboxamide (Example 132) (0.500 g, 1.052 mmol) in MeOH (6 mL) was added palladium hydroxide, (20 wt % Pd (dry basis) on carbon, wet, degussa type) (0.148 g, 1.052 mmol). The resulting mixture was then stirred at rt under H2 overnight. The resulting mixture was filtered through Celite® brand filter agent and the Celite® filter agent was washed with MeOH (2×3 mL). The combined filtrates were concentrated and the mixture was dissolved in DMSO (3 mL). The mixture was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the desired product, which was dissolved in MeOH (2 mL). The solution was washed through PL_HCO3 MP-SPE resin and the resin was washed with MeOH (2×2 mL). The combined filtrates were concentrated and dried in vacuo to give the title compound as a yellow solid. 1H NMR (400 MHz, MeOH) δ ppm 8.94 (d, J=4.1 Hz, 1H), 8.22 (dd, J=8.0, 1.0 Hz, 1H), 7.50-7.70 (m, 5H), 6.94-7.02 (m, 3H), 6.90 (s, 1H), 3.24-3.31 (m, 2H), 2.78 (t, J=6.4 Hz, 2H), 1.86-1.99 (m, 2H). MS (ESI pos. ion) m/z: 480.2 (M+H).

Workup

  1. filtrationThe resulting mixture was filtered through Celite® brand
  2. filtrationfilter agent
  3. filtrationthe Celite® filter agent
  4. washwas washed with MeOH (2×3 mL)
  5. concentrationThe combined filtrates were concentrated
  6. dissolutionthe mixture was dissolved in DMSO (3 mL)
  7. customThe mixture was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA)

Sources & evidence

ORD record
ord-3cc1af742e8446e08cde64ad4c83dfb3
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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