Hydrochloric Acid → HCID 178496280, compound

HRID 1805583Notes

Reaction equation

HRID 1805583 reaction equation
[N:1]([O-])=O.[Na+].[F:5][C:6]1[C:12]([F:13])=[C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:10]=[CH:9][C:7]=1[NH2:8].Cl.[CH3:21][O:22][CH2:23][C:24](=[O:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27].CC([O-])=O.[Na+].[OH-].[Na+]>O.CO>[F:5][C:6]1[C:12]([F:13])=[C:11]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[CH:10]=[CH:9][C:7]=1[NH:8][N:1]=[C:25]([C:24](=[O:30])[CH2:23][O:22][CH3:21])[C:26]([O:28][CH3:29])=[O:27]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 58072523HCID 58072523, compound

Product 1

HCID 178496280HCID 178496280, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of NaNO2 (3.4 g, 49 mmol) in H2O (10 mL) was added dropwise at 0° C. to a mixture of 2,3-difluoro-4-morpholin-4-ylaniline (8.7 g, 41 mmol) and 6 M HCl aqueous solution (41 mL, 244 mmol). After stirring for 15 min, the resulting aqueous solution was added to a suspension of methyl 4-methoxyacetoacetate (5.2 mL, 41 mmol) and NaOAc (14.3 g, 244 mmol) in MeOH (40 mL) pre-cooled at 0° C. The mixture was adjusted to pH 7 with 1 M NaOH aqueous solution (200 mL). The precipitate was collected by filtration, washed with water and dried at room temperature to give the title compound (4.7 g, 31% yield) as a red solid: LC-MS (ESI) m/z 372 [M+H]+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried at room temperature

Sources & evidence

ORD record
ord-a39175d57a304dd39b66c3de0f377335
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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