Water → HCID 18463542, compound

HRID 2231111Notes

Reaction equation

HRID 2231111 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[NH:4][C:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([CH3:24])[CH:17]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11](SC)=[CH:10][CH:9]=2)[N:7]=1.O[O:28][S:29]([O-:31])=O.[K+].O1CCC[CH2:34]1.O>CO>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:5]2[N:4]=[C:3]([C:2]([F:26])([F:25])[F:1])[NH:7][C:6]=2[C:8]2[CH:13]=[CH:12][C:11]([S:29]([CH3:34])(=[O:31])=[O:28])=[CH:10][CH:9]=2)=[CH:17][C:18]=1[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 178489082HCID 178489082, compound

Product 1

HCID 18463542HCID 18463542, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized according to the procedure of Example 41, Step 4 using the product of Step 3 (1 g, 2.6 mmol) and Oxone®(4 g, 6.6 mmol) in methanol (20 ml), tetrahydrofuran (10 ml) and water (5 ml). The crude product was purified by chromatography on silica gel using 50% ethyl acetate in toluene as the eluent to give 610 mg (75%) of the desired product as a crystalline solid: mp 265-267° C. Anal. Calc'd. for C19H17N2F3O3S (MW 410.41): C, 55.60; H, 4.18; N, 6.83; S, 7.81. Found: C, 55.69; H, 4.28; N. 6.70; S, 8.07.

Workup

  1. customThe title compound was synthesized
  2. customThe crude product was purified by chromatography on silica gel using 50% ethyl acetate in toluene as the eluent

Sources & evidence

ORD record
ord-d4f8b83e75f74b28bcf6f6c40467b7bf
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

Loading…