Water → HCID 21948133, compound

HRID 2183802Notes

Reaction equation

HRID 2183802 reaction equation
[OH2:1].[O-2:2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3].O.[NH:20]([C:27]1[N:28]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:29]2[C:34]([C:35](=[O:37])[CH:36]=1)=[C:33]([C:38]([F:41])([F:40])[F:39])[CH:32]=[C:31]([S:42][CH2:43][CH2:44][CH2:45][CH3:46])[N:30]=2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.OOS([O-])=O.[K+]>C(Cl)(Cl)Cl>[NH:20]([C:27]1[N:28]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:29]2[C:34]([C:35](=[O:37])[CH:36]=1)=[C:33]([C:38]([F:40])([F:41])[F:39])[CH:32]=[C:31]([S:42]([CH2:43][CH2:44][CH2:45][CH3:46])(=[O:2])=[O:1])[N:30]=2)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 21948180HCID 21948180, compoundHCID 23707502Potassium hydroxy sulfiteHCID 71586775Bentonite

Product 1

HCID 21948133HCID 21948133, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of montmorillonite K10 (107.5 mg) in CHCl3 was added 13 uL of water. 2-anilino-7-(butylsulfanyl)-1-phenyl-5-(trifluoromethyl)-1,8-naphthyridin-4(1H)-one (25 mg, 0.06 mmol) was then added followed by oxone (85.2 mg, 0.14 mmol). The reaction was allowed to stir for 24 h at room temperature. After 24 h the solution was bright bluish-green in color and was filtered and washed with copious amounts of CHCl3. The filtrate was then concentrated in vacuo. Silica gel flash chromatography using 3:1 Hex:EtOAc provided 2-anilino-7-(butylsulfonyl)-1-phenyl-5-(trifluoromethyl)-1,8-naphthyridin-4(1H)-one as a yellow oil (13.8 mg, 46%): LCMS RT: 3.14, MH+502.2.

Workup

  1. waitAfter 24 h the solution was bright bluish-green in color
  2. filtrationwas filtered
  3. washwashed with copious amounts of CHCl3
  4. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-16803b44ab62499090b2b76bd6fb3bf3
Source dataset
uspto-grants-2005_05
Patent number
US06900205B2

Reaction notes

Loading…