Potassium Phosphate, Tribasic → HCID 71144235, compound

HRID 509424Notes

Reaction equation

HRID 509424 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:13]([NH:21][C:22]([C:24]2[CH:25]=[CH:26][C:27]([N+:38]([O-])=[O:39])=[C:28]([N:30]([CH3:37])[C:31](=[O:36])[C:32]([O:34]C)=O)[CH:29]=2)=[O:23])[C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C@@H:13]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=2)[NH:21][C:22]([C:24]2[CH:29]=[C:28]3[C:27](=[CH:26][CH:25]=2)[N:38]([OH:39])[C:32](=[O:34])[C:31](=[O:36])[N:30]3[CH3:37])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:10])([F:12])[F:11]

Participants

4

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 71143970HCID 71143970, compound

Product 1

HCID 71144235HCID 71144235, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 2-((5-(((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)carbamoyl)-2-nitrophenyl)(methyl)amino)-2-oxoacetate (0.500 g, 0.880 mmol) in MeOH (3 mL, Aldrich), was added palladium, 10 wt. % (dry basis) on activate carbon, wet, degussa type (0.047 g, 0.440 mmol, Aldrich). The resulting mixture was stirred at room temperature under hydrogen (balloon) for 4 h. The mixture was filtered through celite and the celite was washed with MeOH (2×10 mL). The combined filtrates were concentrated in vacuo. Dioxane (3.00 mL, Aldrich) and water (1 mL) were added, followed by potassium phosphate (0.560 g, 2.64 mmol, Strem Chemical). The mixture was heated at 90° C. for 18 h. The mixture was then cooled to room temperature and filtered. The solid was washed with water (2×30 mL) and dried in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.37 (d, J=7.8 Hz, 1H), 8.47 (d, J=4.5 Hz, 1H), 7.93 (br. s., 1H), 7.74-7.84 (m, 3H), 7.55-7.67 (m, 2H), 7.50 (dt, J=8.5, 4.3 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 6.78 (d, J=7.8 Hz, 1H), 3.52-3.66 (m, 3H). MS (ESI, positive ion) m/z: 523 (M+H).

Workup

  1. dry with materialpalladium, 10 wt. % (dry basis) on activate carbon
  2. filtrationThe mixture was filtered through celite
  3. washthe celite was washed with MeOH (2×10 mL)
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. additionDioxane (3.00 mL, Aldrich) and water (1 mL) were added
  6. temperatureThe mixture was heated at 90° C. for 18 h
  7. temperatureThe mixture was then cooled to room temperature
  8. filtrationfiltered
  9. washThe solid was washed with water (2×30 mL)
  10. customdried in vacuo

Sources & evidence

ORD record
ord-ba43dd361cb5424480b6de1d252a1316
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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