Hydrochloric Acid → (R)-5-ethyl-6-(1-methyl-2-(pyrrolidin-2-yl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 1481719Notes

Reaction equation

HRID 1481719 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[N:14]([CH3:36])[C:15]2[C:20]([CH:21]=1)=[CH:19][C:18]([C:22]1[C:31]([CH2:32][CH3:33])=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[C:24]([O:34]C)[N:23]=1)=[CH:17][CH:16]=2)=O)(C)(C)C.Cl>>[CH2:32]([C:31]1[CH:30]=[C:25]([C:26]([OH:28])=[O:27])[C:24](=[O:34])[NH:23][C:22]=1[C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:36])[C:13]([C@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)=[CH:21]2)[CH3:33]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 71291891(R)-Methyl 6-(2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1-methyl-1H-indol-5-yl)-5-ethyl-2-methoxynicotinate

Product 1

HCID 71285019(R)-5-ethyl-6-(1-methyl-2-(pyrrolidin-2-yl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidYield 107.3%

Procedure

(R)-Methyl 6-(2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1-methyl-1H-indol-5-yl)-5-ethyl-2-methoxynicotinate (0.190 g, 0.38 mmol) was heated with 6M HCl (2.0 mL) at 80° C. for 2.5 h until complete conversion to the product was observed by LC/MS. HCl was removed under reduced pressure, residue triturated with Et2O and solid was collected by filtration. (R)-5-ethyl-6-(1-methyl-2-(pyrrolidin-2-yl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (0.149 g, 96%) was obtained as yellow solid.

Workup

  1. customHCl was removed under reduced pressure, residue
  2. customtriturated with Et2O and solid
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-bc84bf5fd83e4196a6201ac3234d6c6f
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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