HCID 89422961, compound → HCID 71285061, compound

HRID 1481754Notes

Reaction equation

HRID 1481754 reaction equation
[CH2:1]([C:4]1[C:5]([OH:38])=[C:6]([C:35]([OH:37])=[O:36])[C:7](=[O:34])[N:8]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=2[O:32][CH3:33])[C:9]=1[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH2:19][N:20]([CH3:22])[CH3:21])=[CH:13]2)[CH:2]=[CH2:3]>CCOC(C)=O.[Pd]>[CH3:33][O:32][C:25]1[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:24]=1[CH2:23][N:8]1[C:9]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([CH2:19][N:20]([CH3:22])[CH3:21])=[CH:13]3)=[C:4]([CH2:1][CH2:2][CH3:3])[C:5]([OH:38])=[C:6]([C:35]([OH:37])=[O:36])[C:7]1=[O:34]

Participants

4

Reactant 1

HCID 89422961HCID 89422961, compound

Product 1

HCID 71285061HCID 71285061, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-allyl-1-(2,4-dimethoxybenzyl)-6-(2-((dimethylamino)methyl)-1H-indol-5-yl)-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid (45 mg, 0.085 mmol), prepared according to the procedure described in Example 164, Steps 1-6, and Pd/C (10 mg, 10%) in EtOAc (1 mL) was stirred under H2 (1 atm) at room temperature for 2 h. The solvent was evaporated and the residue was chromatographed (0-2.5% MeOH in CH2Cl2) to give the intermediate of 1-(2,4-dimethoxybenzyl)-6-(2-((dimethylamino)methyl)-1H-indol-5-yl)-4-hydroxy-2-oxo-5-propyl-1,2-dihydropyridine-3-carboxylic acid. LC-MS 489.2 [M+H]+, RT 1.17 min. This intermediate was stirred in TFA (0.5 mL) and TIPS-H (0.5 mL) at room temperature for 15 h, and then the mixture was concentrated to dryness. The residue was dissolved in CH2Cl2 (0.5 mL), then HCl (2.0M in Et2O, 1.0 mL) was added. The precipitate was collected by filtration and washed by ether to afford the title compound as an off-white solid (15 mg, 44% over 2 steps).

Workup

  1. customprepared
  2. customThe solvent was evaporated
  3. customthe residue was chromatographed (0-2.5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-72c1ba6c28ba4e0390042c2615b20646
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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