Pyridine → HCID 66880351, compound

HRID 2094445Notes

Reaction equation

HRID 2094445 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([F:14])([F:13])[O:7][C:8]2([F:12])[F:11])=[CH:4][C:3]=1[OH:15].[C:16](O)(=[O:23])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[F:13][C:6]1([F:14])[C:5]2[C:9](=[CH:10][C:2]([NH:1][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:3]([OH:15])[CH:4]=2)[C:8]([F:11])([F:12])[O:7]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 5922Isonicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 58148233HCID 58148233, compound

Product 1

HCID 66880351HCID 66880351, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.0 g of 6-amino-1,1,3,3-tetrafluoro-5-hydroxy-1,3-dihydroisobenzofuran, 1.1 g of isonicotinic acid, 2.23 g of WSC and 15 ml of pyridine was stirred while heating at 80° C. for three hours. The reaction mixture was cooled to room temperature, and then water was poured into the reaction mixture. Precipitated solid was filtered and washed with water and dried under reduced pressure to give 1.34 g of N-(1,1,3,3-tetrafluoro-6-hydroxy-1,3-dihydroisobenzofuran-5-yl)isonicotinamide.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customPrecipitated solid
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-2967de37dcf44571a860fc6da9b173f3
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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