HCID 70975986, compound → HCID 70975814, compound

HRID 535616Notes

Reaction equation

HRID 535616 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][N:12]2[N:21]=[C:20]([S:22]([C:25]3[CH:30]=[CH:29][N+:28]([O-])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:32])=[O:10])=[CH:4][CH:3]=1>CO.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][N:12]2[N:21]=[C:20]([S:22]([C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)(=[O:23])=[O:24])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:32])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 70975986HCID 70975986, compound

Product 1

HCID 70975814HCID 70975814, compoundYield 18.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product from Example 196 (10 mg, 0.021 mmol) was treated with 10% Pd/C (5 mg) in MeOH (5 mL) under H2 (1 atm) for 12 hrs. The mixture was filtered, and washed with MeOH, concentrated, and the resulting residue was purified by HPLC (conditions from Example 10C) to afford 1.8 mg of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.97-11.79 (br s, 1H), 8.96 (dd, J=4.5, 1.6, 2H), 8.52 (d, J=8.1, 1H), 8.39 (d, J=7.1, 1H), 8.12 (dd, J=12.0, 4.9, 1H), 8.03 (t, J=7.2, 1H), 7.96 (dd, J=4.5, 1.6, 2H), 7.41 (d, J=8.5, 2H), 7.29 (d, J=8.4, 2H), 3.68 (s, 2H); MS (ESI+) M/Z 455 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with MeOH
  3. concentrationconcentrated
  4. customthe resulting residue was purified by HPLC (conditions from Example 10C)

Sources & evidence

ORD record
ord-61c815c40b0e4e8192259ee6b9d49f23
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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