Trifluoroacetic anhydride → HCID 75151423, compound

HRID 2039688Notes

Reaction equation

HRID 2039688 reaction equation
[CH3:1][C:2]1[C:3]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH:23][C:24](=O)OC(C)(C)C)[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][S:5][N:6]=1.[H-].[Na+].I[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:24]([NH:23][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:16][O:15][N:14]=[C:7]([C:3]2[C:2]([CH3:1])=[N:6][S:5][N:4]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:22]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

7

Reactant 5

HCID 9845Trifluoroacetic anhydrideHCID 125271-IodohexaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 86659839HCID 86659839, compound

Product 1

HCID 75151423HCID 75151423, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of tert-butyl {6-[({[(4-methyl-1,2,5-thiadiazol-3-yl)(phenyl)methylene]-amino}oxy)methyl]pyridin-2-yl}carbamate (104 mg, 0.24 mmol) in dry DMF (5 mL) was added sodium hydride (60 wt.-% in mineral oil, 11 mg, 0.27 mmol). After stirring at room temperature for 15 min, 1-iodohexane (62 mg, 0.29 mmol) was added, and the mixture stirred at room temperature for 16 h. After dropwise addition of trifluoroacetic anhydride (1 mL, 13 mmol), the mixture was stirred at 50° C. for 8 h. The cooled reaction mixture was poured into sat. aq. NaHCO3 (40 mL), extracted with ethyl acetate (2×30 mL), the organic layer was washed with water, dried (MgSO4) and concentrated in vacuo. Purification on silica gel afforded N-hexyl-6-[({[(4-methyl-1,2,5-thiadiazol-3-yl)(phenyl)methylene]amino}-oxy)methyl]pyridin-2-amine as an orange oil [79 mg, yield 75%; HPLC/MS: m/z=410 (M+H); log P(HCOOH)=3.11].

Workup

  1. stirringthe mixture stirred at room temperature for 16 h
  2. stirringthe mixture was stirred at 50° C. for 8 h
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate (2×30 mL)
  5. washthe organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification on silica gel

Sources & evidence

ORD record
ord-ca456098792942b59794f3c5c73452cb
Source dataset
uspto-grants-2013_11
Patent number
US08580799B2

Reaction notes

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