Water → HCID 67954591, compound

HRID 714414Notes

Reaction equation

HRID 714414 reaction equation
[Na].[F:2][C:3]1[C:4]([CH3:18])=[C:5]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[NH:11])[CH:6]=[CH:7][CH:8]=1.C([O:21][CH:22]=[C:23]([C:29](OCC)=O)[C:24]([O:26]CC)=[O:25])C.O.C(=O)(O)[O-].[Na+]>C(#N)C>[F:2][C:3]1[C:4]([CH3:18])=[C:5]([N:9]2[C:22](=[O:21])[C:23]([C:24]([OH:26])=[O:25])=[CH:29][N:11]=[C:10]2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 6871Diethyl (ethoxymethylene)malonateHCID 516892Sodium BicarbonateHCID 178429746HCID 178429746, compound2×

Product 1

HCID 67954591HCID 67954591, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-(3-fluoro-2-methylphenyl)benzenecarboximidamide sodium salt (1:1) (i.e. the product from Example 5, Step A) (51.0 g, 200 mmol) in acetonitrile (300 mL) was added diethyl ethoxymethylenemalonate (44.04 g, 200 mmol). The reaction was stirred at room temperature for 30 min followed by the addition of water (3.6 mL, 200 mmol). The reaction was then stirred for another 30 min Water (100 mL) was added to the residue, followed by a saturated solution of sodium bicarbonate (300 mL), and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid until the pH was 1-2, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure to provide a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a off-white solid (18 g).

Workup

  1. additionwas added to the residue
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto provide a solid, which
  7. washwas washed with diethyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-d8c473e7041e4bb19b108ca74984f389
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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