Tetrahydrofuran → HCID 58148110, compound

HRID 1913602Notes

Reaction equation

HRID 1913602 reaction equation
[F:1][C:2]1([F:23])[C:10]2[C:5](=[CH:6][C:7]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:8](O)[CH:9]=2)[C:4]([F:22])([F:21])[O:3]1.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O.C1(C)C=CC=CC=1>[F:21][C:4]1([F:22])[C:5]2[C:10](=[CH:9][C:8]3[O:20][C:13]([C:14]4[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=4)=[N:12][C:7]=3[CH:6]=2)[C:2]([F:23])([F:1])[O:3]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 66880351HCID 66880351, compound

Product 1

HCID 58148110HCID 58148110, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a mixture of 1.34 g of N-(1,1,3,3-tetrafluoro-6-hydroxy-1,3-dihydroisobenzofuran-5-yl)isonicotinamide, 10 ml of tetrahydrofuran and 1.07 g of triphenylphosphine, 2.67 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature. After 30 minutes, 1.07 g of triphenylphosphine was added, 2.67 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise thereto and stirred for further two hours. Water was added thereto, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and the resultant solid was recrystallized to give 0.14 g of 5,5,7,7-tetrafluoro-2-pyridin-4-yl-5,7-dihydro-furo[3′,4′:4,5]benzo[1,2-d]oxazole (hereinafter, referred to as “active compound 16”).

Workup

  1. additionwas added dropwise at room temperature
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe resultant solid was recrystallized

Sources & evidence

ORD record
ord-6a8bdeaf6e6741799dc576bc58a25ca9
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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