Water → HCID 117864562, compound

HRID 1486322Notes

Reaction equation

HRID 1486322 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[O:23][CH2:24][C:25]1[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=1[F:32].[C:33]([O:38][CH2:39][CH3:40])(=[O:37])[C:34]#[C:35][CH3:36].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:39]([O:38][C:33]([C:34]1[C:35]([CH3:36])=[N:14][N:15]2[C:16]([O:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=3[F:32])=[CH:17][C:18]([O:21][CH3:22])=[CH:19][C:20]=12)=[O:37])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 117857848HCID 117857848, compound

Product 1

HCID 117864562HCID 117864562, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.99 g (6.15 mmol, 72% purity) of 1-amino-2-[(2,6-difluorobenzyl)oxy]-4-methoxypyridinium 2,4,6-trimethylbenzenesulphonate (Example 161A) in 70 ml of N,N-dimethylformamide was admixed with 1.38 g (12.31 mmol) of ethyl 2-butynoate (CAS: 4341-76-8) and 2.55 g (18.46 mmol) of potassium carbonate. The reaction mixture was stirred at room temperature for 18 hours and added dropwise to 150 ml of water. The resulting precipitate was filtered off and dried under reduced pressure, which gave 477 mg (12% yield, 57% purity) of product.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customdried under reduced pressure, which
  3. customgave 477 mg (12% yield, 57% purity) of product

Sources & evidence

ORD record
ord-419694d898b04610b8df69525a0c1d11
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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