Hydrochloric Acid → 5-Bromo-6-(difluoromethyl)-N-(2-methoxy-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 512471Notes

Reaction equation

HRID 512471 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([O:14]C)=O)[C:5](=[O:11])[NH:6][C:7]=1[CH:8]([F:10])[F:9].[NH2:16][CH:17]([CH3:21])[CH2:18][O:19][CH3:20].Cl>>[Br:1][C:2]1[CH:3]=[C:4]([C:12]([NH:16][CH:17]([CH3:21])[CH2:18][O:19][CH3:20])=[O:14])[C:5](=[O:11])[NH:6][C:7]=1[CH:8]([F:9])[F:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 123458MethoxyisopropylamineHCID 69236839Methyl 5-bromo-6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 598282465-Bromo-6-(difluoromethyl)-N-(2-methoxy-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Procedure

At room temperature, 334 mg (1.19 mmol) of methyl 5-bromo-6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate in 3.3 ml (41 mmol) of 2-amino-1-methoxypropane were stirred for 14 h. The pH was then adjusted to 2 by addition of 1N hydrochloric acid, and the mixture was extracted with dichloromethane. Drying and concentration of the extract gave 360 mg (89% of theory) of the product.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customDrying
  3. customconcentration of the extract gave 360 mg (89% of theory) of the product

Sources & evidence

ORD record
ord-e350376827c84488bbd92e7b3b9f3f99
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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