HCID 20723806, compound → HCID 86646915, compound

HRID 2063267Notes

Reaction equation

HRID 2063267 reaction equation
OC1O[N:5]=[N+:4]2[CH2:7][S:8][CH2:9][C:3]=12.[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[C:18]#[C:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([Cl:26])[N:21]=1>C1(C)C=C(C)C=C(C)C=1>[Cl:26][C:22]1[N:21]=[C:20]([C:19]2[C:18]([C:12]3[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:11]=3[F:10])=[N:5][N:4]3[C:3]=2[CH2:9][S:8][CH2:7]3)[CH:25]=[CH:24][N:23]=1

Participants

4

Reactant 2

HCID 20723806HCID 20723806, compoundHCID 178519226HCID 178519226, compound

Product 1

HCID 86646915HCID 86646915, compound

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Procedure

A solution of 3-hydroxy-4H,6H-thiazolo[3,4-c][1,2,3]oxadiazol-7-ium, inner salt (0.63 g, 4.3 mmol) (prepared from thiazolidine-4-carboxylic acid by nitrosation and treatment with trifluoroacetic anhydride as described in Sutcliffe et al. Tetrahedron 2000, 24, 10011-10021) and 4-[2-(2,4-difluorophenyl)ethynyl)-2-chloropyrimidine (1.0 g, 4.0 mmol) in mesitylene (15 mL) was heated at 155-160° C. under nitrogen for 48 h. The reaction mixture was concentrated under reduced pressure. The crude residue was purified by medium pressure liquid chromatography using 0 to 50% ethyl acetate in hexanes as eluant to give 0.09 g of the title compound as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe crude residue was purified by medium pressure liquid chromatography

Sources & evidence

ORD record
ord-f9df9fbdfc514050b54bdbe83634531c
Source dataset
uspto-grants-2012_10
Patent number
US08288375B2

Reaction notes

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