HCID 67419657, compound → HCID 53380286, compound

HRID 1056881Notes

Reaction equation

HRID 1056881 reaction equation
C([O:8][C:9]1[C:10](=[O:29])[CH:11]=[C:12]([NH:27][CH3:28])[N:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:17]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=[C:15]([N:13]2[CH:14]=[C:9]([OH:8])[C:10](=[O:29])[CH:11]=[C:12]2[NH:27][CH3:28])[CH:16]=1

Participants

4

Reactant 1

HCID 67419657HCID 67419657, compound

Product 1

HCID 53380286HCID 53380286, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(benzyloxy)-1-(biphenyl-3-yl)-2-(methylamino)pyridin-4(1H)-one (1.3 Ig, 3.43 rnmol) 10% Pd/C (150 mg) in MeOH (200 mL) was stirred under an ¾ balloon for 2 h. After this time, LCMS indicated that the reaction was complete. The catalyst was filtered and washed with MeOH (4×50). The combined MeOH solution was concentrated to give 1-(biphenyl-3-yl)-5-hydroxy-2-(methylamino)pyridin-4(1H)-one as slightly yellow solid. ′H NMR (500 MHz, DMSO): δ 7.84-7.81 (m, 1H); 7.78-7.74 (mf 2H); 7.70-7.62 (m, 2H); 7.52-7.46 (m, 2H); 7.42-7.36 (m, 2H); 6.93 (s, 1H); 5.42-5.32 (m, 2H); 2.58 (d, J=4.7 Hz, 3H). LC/MS (M+H), 293. HRMS Calculated for (Ci8H,6N2O2+H)+ 293.1285. found 293.1285.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with MeOH (4×50)
  3. concentrationThe combined MeOH solution was concentrated

Sources & evidence

ORD record
ord-2cf12768f5a642ebbbdf85c1e4677299
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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