Water → HCID 117859492, compound

HRID 1486235Notes

Reaction equation

HRID 1486235 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[O:22][CH2:23][C:24]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=1[F:31].[C:32]([O:37][CH2:38][CH3:39])(=[O:36])[C:33]#[C:34][CH3:35].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:30][C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([F:31])[C:24]=1[CH2:23][O:22][C:16]1[N:15]2[N:14]=[C:34]([CH3:35])[C:33]([C:32]([O:37][CH2:38][CH3:39])=[O:36])=[C:20]2[CH:19]=[C:18]([CH3:21])[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 117857852HCID 117857852, compound

Product 1

HCID 117859492HCID 117859492, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.62 g (3.60 mmol, 1.0 eq.) of 1-amino-2-[(2,6-difluorobenzyl)oxy]-4-methylpyridinium 2,4,6-trimethylbenzenesulphonate from Example 2A were dissolved in 36 ml of DMF, and 0.84 ml (7.19 mmol, 2.0 eq.) of ethyl but-2-ynoate [CAS No: 4341-76-8] were added. 0.994 g (7.19 mmol, 2.0 eq.) of potassium carbonate was added and the mixture was stirred at RT for 1.5 h. Subsequently, the mixture was poured onto 150 ml of water and stirred briefly, and the precipitated solids were filtered off, washed with water and dried. 440 mg of the title compound were obtained (45% of theory, 87%).

Workup

  1. stirringstirred briefly
  2. filtrationthe precipitated solids were filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-4b1c6f2a783f4479a8cc2cc386a19b2b
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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