Pyridine → HCID 66880351, compound

HRID 1913690Notes

Reaction equation

HRID 1913690 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-72c2d81d27774cf092d18abb2001c047
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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