Acetonitrile → HCID 86591940, compound

HRID 2113231Notes

Reaction equation

HRID 2113231 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:3][CH:2]=1.O.O.O.[F:17][C:18]([F:26])([F:25])[C:19]([C:21]([F:24])([F:23])[F:22])=[O:20].C(#N)C>C1C=CC=CC=1>[F:17][C:18]([F:26])([F:25])[C:19]([C:11]1[S:10][C:9]([NH:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[N:13][CH:12]=1)([OH:20])[C:21]([F:24])([F:23])[F:22]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 36719Hexafluoroacetone trihydrateHCID 29790482HCID 29790482, compound

Product 1

HCID 86591940HCID 86591940, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

Molecular sieves powder (4A) (1 g) was added to a mixture of crude intermediate N-(pyridin-4ylmethyl)-1,3-thiazol-2-amine prepared above (2.5 g 13 mmol) and hexafluoroacetone trihydrate (4 g, 18.1 mmol) in benzene (3 ml). The mixture was heated at 80° C. for 24 h. Acetonitrile was added and mixture was filtered. Solvent was evaporated under reduced pressure. The residue was chromatographed on silica gel, eluting with a 95:5 mixture of CHCl3 and CH3OH, to afford the title compound as an orange solid (1.1 g). 1H NMR (DMSO-d6) δ 4.3 (d, 2H), 7.10 (s, 1H), 7.42 (d, 2H); 7.78 (d, 2H), 8.45 (brs, 1H), 8.82 (brs, 1H); ESIMS: m/z 356 (M−H).

Workup

  1. filtrationmixture was filtered
  2. customSolvent was evaporated under reduced pressure
  3. customThe residue was chromatographed on silica gel
  4. washeluting with a 95:5 mixture of CHCl3 and CH3OH

Sources & evidence

ORD record
ord-2505096012264699b361f53735ded911
Source dataset
uspto-grants-2009_04
Patent number
US07524969B2

Reaction notes

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