Hydrochloric Acid → 4-hydroxy-5-methyl-6-(2-(methylamino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid hydrochloride

HRID 1481797Notes

Reaction equation

HRID 1481797 reaction equation
C([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH:35]([NH:37][CH3:38])[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[C:22]([CH3:39])=[C:21]([O:40]CC2C=CC=CC=2)[C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])C1C=CC=CC=1.[ClH:48]>CO.[Pd]>[ClH:48].[OH:40][C:21]1[C:22]([CH3:39])=[C:23]([C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH:35]([NH:37][CH3:38])[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[NH:24][C:9](=[O:8])[C:10]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71284780benzyl 2,4-bis(benzyloxy)-5-methyl-6-(2-(methylamino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)nicotinate

Product 1

HCID 712845334-hydroxy-5-methyl-6-(2-(methylamino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid hydrochlorideYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

The intermediate from Step 2 (70 mg, 0.11 mmol) was dissolved in MeOH (2 mL). To the solution was added 10% Pd/C (20 mg) and 3 N HCl in MeOH (0.1 mL). The mixture was stirred under H2 (1 atm) at room temperature for 16 h. The mixture was filtered through a 5 μm cartridge. The filtrate was concentrated, leaving the product (21 mg, 49%) as an off white powder.

Workup

  1. filtrationThe mixture was filtered through a 5 μm cartridge
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c9ba8f07d29d4c1aa39698fe1e2d0d62
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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