Tetrahydrofuran → 3-{9-[8-(2,2,2-Trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthen-3-yl}-4H-[1,2,4]thiadiazol-5-one

HRID 1987945Notes

Reaction equation

HRID 1987945 reaction equation
O[NH:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[C:19]3[CH2:25][CH:24]4[N:26]([C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH:21]([CH2:22][CH2:23]4)[CH2:20]3)[C:10]3[C:15]([O:16][C:17]=2[CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[NH:4].C1N=CN([C:38](N2C=NC=C2)=[S:39])C=1.C1C[O:48]CC1>O>[F:29][C:28]([F:31])([F:30])[C:27]([N:26]1[CH:24]2[CH2:23][CH2:22][CH:21]1[CH2:20][C:19](=[C:9]1[C:8]3[CH:7]=[CH:6][C:5]([C:3]4[NH:2][C:38](=[O:48])[S:39][N:4]=4)=[CH:18][C:17]=3[O:16][C:15]3[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:25]2)=[O:32]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 802641,1'-ThiocarbonyldiimidazoleHCID 178513222HCID 178513222, compound

Product 1

HCID 1359999753-{9-[8-(2,2,2-Trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthen-3-yl}-4H-[1,2,4]thiadiazol-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of compound 6a (0.0417 g, 0.094 mmol) and TCDI (0.025 g, 0.14 mmol) in THF (2 mL) was stirred at room temperature for 45 min. The mixture was diluted with H2O (2 mL) and extracted with EtOAc (3×5 mL). The combined organic extracts were washed with H2O (15 mL), dried (MgSO4), and concentrated. The residue was dissolved in THF (2 mL). Boron trifluoride diethyl etherate was added to the solution, and the resulting mixture was stirred at room temperature for 1 h. The mixture was diluted with H2O (2 mL) and extracted with EtOAc (3×5mL). The organic layers were dried (MgSO4), and concentrated. The resultant compound 9a was used in the next reaction without further purification. MS m/z (MH+) 485.8.

Workup

  1. extractionextracted with EtOAc (3×5 mL)
  2. washThe combined organic extracts were washed with H2O (15 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in THF (2 mL)
  6. additionBoron trifluoride diethyl etherate was added to the solution
  7. stirringthe resulting mixture was stirred at room temperature for 1 h
  8. additionThe mixture was diluted with H2O (2 mL)
  9. extractionextracted with EtOAc (3×5mL)
  10. dry with materialThe organic layers were dried (MgSO4)
  11. concentrationconcentrated
  12. customThe resultant compound 9a was used in the next reaction without further purification

Sources & evidence

ORD record
ord-2567296273fa4e6985ddcf045f8e1231
Source dataset
uspto-grants-2009_06
Patent number
US07553850B2

Reaction notes

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