(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 58387952, compound

HRID 2079954Notes

Reaction equation

HRID 2079954 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[CH3:14][O:15][C:16](=[O:27])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24]O)=[N:19][C:18]=1[NH2:26]>ClCCl>[CH3:14][O:15][C:16](=[O:27])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][F:11])=[N:19][C:18]=1[NH2:26]

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 58387955HCID 58387955, compound

Product 1

HCID 58387952HCID 58387952, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (bis(2-methoxyethyl)amino)sulfur trifluoride (2.39 g, 10.8 mmol) in dichloromethane (30 mL) was cooled with a dry ice-methanol bath, and 2-amino-6-(2-hydroxyethyl)-nicotinic acid methyl ester (50 mg, 0.255 mmol) was added thereto dropwise. After dropwise addition the cold bath was immediately removed, and the solution was gradually allowed to room temperature. Water and ethyl acetate were added to the reaction solution, which was then partitioned. The organic layer was separated, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography, and the title compound (4 mg, 0.020 mmol, 7.9%) was obtained as a white solid.

Workup

  1. additionAfter dropwise addition the cold bath
  2. customwas immediately removed
  3. customwas gradually allowed to room temperature
  4. additionWater and ethyl acetate were added to the reaction solution, which
  5. customwas then partitioned
  6. customThe organic layer was separated
  7. customthe solvent was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb8ac51043154bfcbcaf2574f8c54f47
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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