Triethylamine → HCID 59654957, compound

HRID 2053450Notes

Reaction equation

HRID 2053450 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11]([OH:19])=[C:10]([C:20]2[O:24][N:23]=[C:22]([CH3:25])[CH:21]=2)[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[O:34](S(C(F)(F)F)(=O)=O)[S:35]([C:38]([F:41])([F:40])[F:39])(=O)=[O:36].CCOC(C)=O>C(Cl)Cl>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11]([O:19][S:35]([C:38]([F:41])([F:40])[F:39])(=[O:36])=[O:34])=[C:10]([C:20]2[O:24][N:23]=[C:22]([CH3:25])[CH:21]=2)[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67749Trifluoromethanesulfonic anhydrideHCID 136018654HCID 136018654, compound

Product 1

HCID 59654957HCID 59654957, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-6-chloro-4-hydroxy-3-(3-methyl-isoxazol-5-yl)-1H-quinolin-2-one (1.00 g, 2.73 mmol) and Et3N (0.57 ml, 4.10 mmol) in 20 ml of DCM under at −78° C. was added Tf2O (0.50 ml, 3.0 mmol) slowly under Ar. The mixture was warmed to rt. Treated with 150 ml of EtOAc, the mixture was washed with H2O (4×50 mL), brine (40 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure gave 1.35 g (99%) of product as a light yellow solid: 1H-NMR (CDCl3; 400 MHz) δ 7.95 (d, 1H, J=2.3 Hz), 7.55 (dd, 1H, J=9.0, 2.3 Hz), 7.27-7.37 (m, 4H), 7.21 (d, 2H, J=8.3 Hz), 7.17 (s, 1H), 5.60 (s, 2H), 2.42 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C21H14ClF3N2O5S, 499.0 (M+H), found 499.0.

Workup

  1. washthe mixture was washed with H2O (4×50 mL), brine (40 mL)
  2. dry with materialdried (Na2SO4)
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-a4e1492b23a5461998d84ed059fc364c
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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