Hydrochloric Acid → HCID 58072528, compound

HRID 1407223Notes

Reaction equation

HRID 1407223 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][C:3]=1[N:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18](=[O:23])[C:17]([C:24]([O:26]C)=[O:25])=[N:16]1.[OH-].[Na+].Cl>CCO>[F:1][C:2]1[C:7]([F:8])=[C:6]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[CH:5]=[CH:4][C:3]=1[N:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18](=[O:23])[C:17]([C:24]([OH:26])=[O:25])=[N:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58072210HCID 58072210, compound

Product 1

HCID 58072528HCID 58072528, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 1-(2,3-difluoro-4-morpholin-4-ylphenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate (4.1 g, 11 mmol) and 2 M NaOH aqueous solution (11 mL, 22 mmol) in EtOH (20 mL) was stirred at room temperature for 16 h. To the mixture was added 1 M HCl aqueous solution (21 mL). The precipitate was collected by filtration and dried over under reduced pressure to give the title compound (3.8 g, 98% yield) as a white solid: 1H NMR (300 MHz, DMSO-d6): δ ppm 3.06-3.23 (4H, m), 3.66-3.82 (4H, m), 3.88 (3H, s), 6.84-7.27 (1H, m), 7.36-7.74 (1H, m), 8.86 (1H, d, J=1.1 Hz), 14.95 (1H, brs). LC-MS (ESI) m/z 368 [M+H]+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried over under reduced pressure

Sources & evidence

ORD record
ord-85d038e807e748e88049a8b280b85d0b
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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