Trifluoroacetic acid → HCID 59580663, compound

HRID 1470427Notes

Reaction equation

HRID 1470427 reaction equation
[F:1][C:2]1[N:3]=[C:4]([C:22]2[CH:23]=[N:24][CH:25]=[C:26]([F:28])[CH:27]=2)[S:5][C:6]=1[N:7](C(OC(C)(C)C)=O)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].FC(F)(F)C(O)=O>ClCCl>[C:11]([O:10][C:8](=[O:9])[NH:7][C:6]1[S:5][C:4]([C:22]2[CH:23]=[N:24][CH:25]=[C:26]([F:28])[CH:27]=2)=[N:3][C:2]=1[F:1])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59580494HCID 59580494, compound

Product 1

HCID 59580663HCID 59580663, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of di(tert-butyl) 4-fluoro-2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate (320 mg, 0.77 mmol) in DCM (7 mL) was added trifluoroacetic acid (TFA) (0.7 mL). The solution was stirred at room temperature for 10 minutes, before quenched slowly with saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane (DCM). The combined organic layer was dried over Na2SO4, filtered and purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give product as a pale yellow solid (166 mg, 68%): mp 188-191° C.; 1H NMR (300 MHz, CDCl3) δ 8.84 (s, 1H), 8.46 (d, J=2.7 Hz, 1H), 7.85 (ddd, J=9.1, 2.6, 1.7 Hz, 1H), 6.92 (br s, 1H), 1.55 (s, 9H); ESIMS m/z 312 (M−1).

Workup

  1. custombefore quenched slowly with saturated NaHCO3 solution
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (DCM)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. custompurified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-73fd4f81ffc64e778e40d3a579194f1f
Source dataset
uspto-grants-2015_04
Patent number
US09006446B2

Reaction notes

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