(Diethylamino)sulfur trifluoride → HCID 136246040, compound

HRID 59539Notes

Reaction equation

HRID 59539 reaction equation
[Cl:1][C:2]1[C:16]([C:17]2[NH:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:18]=2)=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[C:9]([CH3:13])([CH3:12])[CH2:10]O)=[C:4]([F:30])[CH:3]=1.CCN(S(F)(F)[F:37])CC>C1COCC1>[Cl:1][C:2]1[C:16]([C:17]2[NH:21][C:20](=[O:22])[N:19]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[N:18]=2)=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[C:9]([CH3:13])([CH3:12])[CH2:10][F:37])=[C:4]([F:30])[CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 136492356HCID 136492356, compound

Product 1

HCID 136246040HCID 136246040, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-chloro-5-(1-(4-chlorophenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (0.150 g, 0.330 mmol) in THF (5.0 mL), DAST (0.079 g, 0.495 mmol) was added at 0-5° C. and stirred at RT for 5-6 h. After completion of the reaction, the reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was separated, concentrated and the obtained crude was purified with column chromatography using basic alumina by eluting with solution of 2% ammonia in 10.0% MeOH:DCM to afford 0.013 g of the desired product. 1H NMR (300 MHz, CDCl3): δ 1.13 (s, 6H), 4.32 (m, 3H), 4.46 (s, 1H), 7.55 (m, 2H), 7.69 (m, 2H), 7.94-7.97 (m, 2H), 8.31 (s, 1H), 12.61 (s, 1H); MS (m/z): 454.25 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mass was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customthe obtained crude
  7. customwas purified with column chromatography
  8. washby eluting with solution of 2% ammonia in 10.0% MeOH

Sources & evidence

ORD record
ord-5a84dcd2ea454eccbf900dde3c266625
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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