HCID 59644531, compound → HCID 10175375, compound

HRID 2252000Notes

Reaction equation

HRID 2252000 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[C:23]3=[C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])[O:25][N:26]=[C:22]3[CH:21]=[CH:20][N:19]=2)[N:9]=[N:8]1>C(OCC)(=O)C.[Pt]>[NH2:26][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([C:10]2[N:9]=[N:8][N:7]([CH2:6][C:5]3[CH:34]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:36]=[C:3]([C:2]([F:41])([F:1])[F:42])[CH:4]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:23]=1[C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[Cl:33])=[O:25]

Participants

4

Reactant 1

HCID 59644531HCID 59644531, compound

Product 1

HCID 10175375HCID 10175375, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Stir a mixture of 4-[1-(3,5-bistrifluoromethylbenzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-3-(2-chlorophenyl)-isoxazolo[4,3-c]pyridine (350 g, 0.583 mol) and 5% Pt—C (35 g) in ethyl acetate (3.5 L) under a H2 (˜5 psi) atmosphere for 20 hours. Filter through hyflo, wash with ethyl acetate (3.5 L) and concentrate to a solid. Dissolve in ethyl acetate (7 L) and add Darco® (600 g). Stir for 2 hours then filter through hyflo. Rinse filter cake with ethyl acetate (3.5 L) and concentrate filtrates to give the title compound. Exact Mass 601.1: mass spectrum (IS): m/z=602.0 (M+1); 1H NMR (250 MHz, CDCl3) 8.0 (d, J=6.0 Hz, 1H), 7.23 (s, 1H), 7.45-7.29 (m, 5H), 7.22 (m, 1H), 7.13-7.03 (m, 2H), 6.96 (m, 1H), 6.90-6.80 (m, 2H), 6.48 (d, J=6.0 Hz, 1H), 7.79 (bs, 2H), 5.31 (s, 2H).

Workup

  1. filtrationFilter through hyflo
  2. washwash with ethyl acetate (3.5 L)
  3. concentrationconcentrate to a solid
  4. dissolutionDissolve in ethyl acetate (7 L)
  5. additionadd Darco® (600 g)
  6. stirringStir for 2 hours
  7. filtrationthen filter through hyflo
  8. washRinse
  9. filtrationfilter cake with ethyl acetate (3.5 L)
  10. concentrationconcentrate filtrates

Sources & evidence

ORD record
ord-51211294d41341c7b9056c756bbb0897
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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