Tert-Butylamine → HCID 71293875, compound

HRID 1747559Notes

Reaction equation

HRID 1747559 reaction equation
[F:1][C:2]([F:38])([F:37])[CH:3]([C:30]1[CH:35]=[CH:34][N+:33]([O-])=[CH:32][CH:31]=1)[O:4][C:5]1[C:14]([N:15](COCC[Si](C)(C)C)[S:16]([CH2:19][CH2:20][CH3:21])(=[O:18])=[O:17])=[N:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1.C([NH2:43])(C)(C)C.C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C(F)(F)F)C=CC=CC=1.O>[NH2:43][C:32]1[CH:31]=[C:30]([CH:3]([O:4][C:5]2[C:14]([NH:15][S:16]([CH2:19][CH2:20][CH3:21])(=[O:18])=[O:17])=[N:13][C:12]3[C:7]([N:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:2]([F:38])([F:37])[F:1])[CH:35]=[CH:34][N:33]=1

Participants

7

Reactant 4

HCID 6385Tert-Butylamine3×HCID 77773Toluene-p-sulphonic anhydride3×HCID 516892Sodium BicarbonateHCID 86678206HCID 86678206, compound

Product 1

HCID 71293875HCID 71293875, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7368(Trifluoromethyl)benzeneSolvent

Procedure

Compound B4 (200 mg, 0.349 mmol) obtained in Step 1 of Example 42 was suspended in benzotrifluoride (10 mL). To the suspension were added tert-butylamine (0.19 mL, 1.7 mmol) and p-toluenesulfonic anhydride (228 mg, 0.698 mmol), and the mixture was stirred at room temperature for 18 hours. To the reaction mixture were added tert-butylamine (0.19 mL, 1.7 mmol) and p-toluenesulfonic anhydride (228 mg, 0.698 mmol) and the mixture was further stirred at room temperature for 18 hours. Further, to the reaction mixture were added tert-butylamine (0.19 mL, 1.7 mmol) and p-toluenesulfonic anhydride (228 mg, 0.698 mmol) and the mixture was further stirred at room temperature for 18 hours. A saturated aqueous sodium bicarbonate solution and water were added to the reaction mixture. Extraction with ethyl acetate and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was dissolved in benzotrifluoride (2.0 mL) and trifluoroacetic acid (2.0 mL) and the solution was stirred at 70° C. for 18 hours. The solvent was evaporated under reduced pressure, and a saturated aqueous sodium bicarbonate solution and water were added to the residue. Extraction with ethyl acetate and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=1/10) to give Compound 45 (83.2 mg, 54% yield).

Workup

  1. stirringthe mixture was further stirred at room temperature for 18 hours
  2. stirringthe mixture was further stirred at room temperature for 18 hours
  3. extractionExtraction with ethyl acetate
  4. dry with materialdrying over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in benzotrifluoride (2.0 mL)
  8. stirringtrifluoroacetic acid (2.0 mL) and the solution was stirred at 70° C. for 18 hours
  9. customThe solvent was evaporated under reduced pressure
  10. additiona saturated aqueous sodium bicarbonate solution and water were added to the residue
  11. extractionExtraction with ethyl acetate
  12. dry with materialdrying over anhydrous sodium sulfate
  13. filtrationAfter filtration
  14. customthe solvent in the filtrate was evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (chloroform/methanol=1/10)

Sources & evidence

ORD record
ord-1cdbb600de0340beada017fdd68290e7
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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