Methanol → HCID 67415874, compound

HRID 1951415Notes

Reaction equation

HRID 1951415 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[NH:16][CH:15]=[CH:14][C:13]=3[NH:12][C:11]([CH3:20])=[C:10]2[C:21]#[N:22])=[C:5]([O:23][CH3:24])[CH:4]=1)#[N:2].FC(F)(F)S(O[CH2:31][CH3:32])(=O)=O.CO>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[N:16][C:17]=3[O:19][CH2:31][CH3:32])[NH:12][C:11]([CH3:20])=[C:10]2[C:21]#[N:22])=[C:5]([O:23][CH3:24])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 67924Ethyl trifluoromethanesulphonateHCID 67418463HCID 67418463, compound

Product 1

HCID 67415874HCID 67415874, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

505 mg (1.58 mmol) of 4-(4-cyano-2-methoxyphenyl)-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carbonitrile are suspended in THF (20 ml), and 1.9 ml (1.9 mmol) of N′″-(tert-butyl)-N,N′,N″-tris[tris(dimethylamino)phosphoranylidene]phosphorimide triamide (phosphazene base P4-t-Bu; 1 M in hexane) are added. Then 240 μl (1.9 mmol) of ethyl trifluoromethanesulfonate are added to the dark red solution. The decolorized solution is stirred for a further 10 min and then mixed with methanol and concentrated. The residue is purified by preparative HPLC to result in 124 mg (21% of theory) of the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-ba202821b6b442a493b4d381f92a74a5
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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