Ethyl trifluoromethanesulphonate → HCID 24798511, compound

HRID 1951413Notes

Reaction equation

HRID 1951413 reaction equation
[C:1]([C:4]1[CH:13]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=2[O:22][C:23]([F:26])([F:25])[F:24])[C:12]2[C:11](=[O:27])[NH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:5]=1[CH3:28])(=[O:3])[CH3:2].FC(F)(F)S(O[CH2:35][CH3:36])(=O)=O.C(=O)(O)[O-].[Na+]>C1COCC1>[C:1]([C:4]1[CH:13]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=2[O:22][C:23]([F:26])([F:25])[F:24])[C:12]2[C:7](=[CH:8][CH:9]=[N:10][C:11]=2[O:27][CH2:35][CH3:36])[NH:6][C:5]=1[CH3:28])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 67924Ethyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 59603017HCID 59603017, compound

Product 1

HCID 24798511HCID 24798511, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.40 g (6.16 mmol) of 4-(3-acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-(trifluoromethoxy)benzonitrile (example 10A) are suspended in 5 ml of abs. THF and, after addition of 6.78 ml (6.78 mmol) of N″′-(tert-butyl)-N,N′,N″-tris[tris(dimethylamino)-phosphoranylidene]phosphorimide triamide (phosphazene base P4-t-Bu; 1 M in hexane), stirred for 5 min. Then 1.32 g (7.40 mmol) of ethyl trifluoromethanesulfonate are added. After stirring for a further 5 min, the mixture is hydrolyzed with saturated sodium bicarbonate solution and extracted twice with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried with sodium sulfate and then concentrated in a rotary evaporator. The residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 3:7). Recrystallization from acetonitrile finally affords 745 mg (29% of theory) of the title compound.

Workup

  1. stirringAfter stirring for a further 5 min
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in a rotary evaporator
  6. customThe residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 3:7)
  7. customRecrystallization from acetonitrile finally affords 745 mg (29% of theory) of the title compound

Sources & evidence

ORD record
ord-406f3b8b1122494887904dcbb1db3783
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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