Acetic Acid → HCID 57586385, compound

HRID 2190316Notes

Reaction equation

HRID 2190316 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[C:17]([Si](C)(C)C)[N:16]=[N:15]2)=[CH:10][CH:9]=1.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[N:14]1([C:11]2[CH:10]=[CH:9][C:8]([C:3]3[N:4]=[C:5]([NH2:7])[S:6][C:2]=3[Cl:1])=[CH:13][CH:12]=2)[CH:18]=[CH:17][N:16]=[N:15]1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 962WaterHCID 2724141Tetrabutylammonium Fluoride2×HCID 57586337HCID 57586337, compound

Product 1

HCID 57586385HCID 57586385, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-4-(4-(4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)phenyl)thiazol-2-amine (0.70 g, 2.0 mmol), prepared in the previous step, in THF (10 mL) at 0° C. was added acetic acid (0.125 mL, 2.2 mmol) and tetrabutylammonium fluoride (2.2 mL, 1 M in THF, 2.2 mmol). The reaction mixture was warmed to room temperature and stirred for 1 h, heated to 40° C. for 2 h, and additional AcOH (0.035 mL, 0.61 mmol) and TBAF (0.60 mL, 1 M in THF, 0.60 mmol) were added. Stirring was continued at 40° C. After 3 h, the reaction mixture was poured into water (300 mL). The precipitate that formed was collected by filtration, washed with water, and dried under high vacuum. Purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes gave 4-(4-(1H-1,2,3-triazol-1-yl)phenyl)-5-chlorothiazol-2-amine.

Workup

  1. temperatureheated to 40° C. for 2 h
  2. stirringStirring
  3. customwas continued at 40° C
  4. waitAfter 3 h
  5. customThe precipitate that formed
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried under high vacuum
  9. customPurification by flash column chromatography on silica gel (
  10. washeluted with 50% to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-58933d9ceae240c68f5afb4601387e90
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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