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

HRID 1481794Notes

Reaction equation

HRID 1481794 reaction equation
[NH2:1][CH:2]1[CH2:46][N:5]2[C:6]3[CH:7]=[CH:8][C:9]([C:13]4[C:28]([CH3:29])=[C:27]([O:30]CC5C=CC=CC=5)[C:16]([C:17]([O:19]CC5C=CC=CC=5)=[O:18])=[C:15]([O:38]CC5C=CC=CC=5)[N:14]=4)=[CH:10][C:11]=3[CH:12]=[C:4]2[CH2:3]1.[ClH:47]>CO.[Pd]>[ClH:47].[NH2:1][CH:2]1[CH2:46][N:5]2[C:6]3[CH:7]=[CH:8][C:9]([C:13]4[NH:14][C:15](=[O:38])[C:16]([C:17]([OH:19])=[O:18])=[C:27]([OH:30])[C:28]=4[CH3:29])=[CH:10][C:11]=3[CH:12]=[C:4]2[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71284437benzyl 6-(2-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-2,4-bis(benzyloxy)-5-methylnicotinate

Product 1

HCID 712849696-(2-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-4-hydroxy-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid hydrochlorideYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

The intermediate from Step 4 (36 mg, 0.06 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 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-0d21195e1604436a8032c56df8a5fe8b
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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