HCID 46221901, compound → HCID 46221905, compound

HRID 400552Notes

Reaction equation

HRID 400552 reaction equation
[NH2:1][C:2]1[C:3]2[C:26]([CH3:28])([CH3:27])[C:25](=[O:29])[NH:24][C:4]=2[N:5]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13](Cl)=[CH:14][CH:15]=3)[C:10]([CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[N:9]2)[N:7]=1>CO.[OH-].[OH-].[Pd+2]>[NH2:1][C:2]1[C:3]2[C:26]([CH3:27])([CH3:28])[C:25](=[O:29])[NH:24][C:4]=2[N:5]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:18][CH2:19][C:20]([F:22])([F:21])[F:23])=[N:9]2)[N:7]=1

Participants

4

Reactant 1

HCID 46221901HCID 46221901, compound

Product 1

HCID 46221905HCID 46221905, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The compound of Example 1 (9 mg, 0.02 mmol) and palladium hydroxide on carbon (20 wt %, 15 mg) in MeOH (ca 10 mL) were stirred under a hydrogen atmosphere (balloon). After stirring for several hours the solution was filtered through celite and concentrated. The residue was purified by preparative TLC using 5% MeOH/DCM as the eluent to give the indicated compound. 1H NMR (500 MHz, DMSO-d6): δ 11.08 (s, 1H); 8.82 (d, J=8.5 Hz, 1H); 7.89 (d, J=8.0 Hz, 1H); 7.53 (t, J=7.8 Hz, 1H); 7.31 (t, J=7.5 Hz, 1H); 6.94 (s, 2H); 3.28-3.21 (m, 2H); 2.89-2.77 (m, 2H); 1.35 (s, 6H). LC4 rt=3.42 min, m/z=391 (M+H).

Workup

  1. filtrationwas filtered through celite
  2. concentrationconcentrated
  3. customThe residue was purified by preparative TLC
  4. customto give the indicated compound
  5. customLC4 rt=3.42 min, m/z=391 (M+H)

Sources & evidence

ORD record
ord-72edc02a52c14905a6aee8ef0e9ad676
Source dataset
uspto-grants-2014_06
Patent number
US08741910B2

Reaction notes

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