Diethyl Ether → HCID 57929906, compound

HRID 1929993Notes

Reaction equation

HRID 1929993 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH:26]2[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]2)[S:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=2)[N:19]=1.C(O)(C(F)(F)F)=O.CCOCC>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[S:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=2)[N:19]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 57929926HCID 57929926, compound

Product 1

HCID 57929906HCID 57929906, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 100 mL flask was charged with tert-butyl 4-(4-(2,4-difluorophenyl)-5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)thiazol-2-yl)piperidine-1-carboxylate (1.05 g, 1.94 mmol, prepared using General Procedure O from Preparation #A.2 and tert-butyl 4-(aminocarbothioyl) tetrahydropyridine-1-(2H)-carboxylate) in DCM (10 mL) to give a yellow solution. To the solution was added TFA (1.50 mL, 19.4 mmol) and the mixture was stirred at ambient temperature. After about 19 h, the reaction was concentrated under reduced pressure to give a yellow oil which was redissolved in DCM and washed sequentially with 10% aqueous NaOH, water, and brine. The organic solution was dried over MgSO4, filtered, and concentrated to dryness under reduced pressure to give a yellow oil. Upon addition of Et2O, a cloudy solution was formed. Concentration of this solution yielded the title compound as a yellow powder (0.65 g, 76%): LC/MS (Table 1, Method a) Rt=1.54 min; MS m/z: 441.2 (M+H)+.

Workup

  1. customto give a yellow solution
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customto give a yellow oil which
  4. washwashed sequentially with 10% aqueous NaOH, water, and brine
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customto give a yellow oil
  9. customa cloudy solution was formed

Sources & evidence

ORD record
ord-f65fc3006f374d2dbf1e46ef05048d26
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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