Diethyl cyanophosphonate → HCID 21993780, compound

HRID 1978410Notes

Reaction equation

HRID 1978410 reaction equation
[N:1]1[CH:2]=[C:3]2[N:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=13)[S:6][C:5]([C:13]([OH:15])=O)=[CH:4]2.Cl.Cl.[C:18]1([CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][CH:29]([CH2:33][NH2:34])[CH2:28]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.P(C#N)(OCC)(OCC)=O.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)CC)C>[C:18]1([CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][CH:29]([CH2:33][NH:34][C:13]([C:5]3[S:6][C:7]4[N:12]5[C:3](=[CH:2][N:1]=[C:11]5[CH:10]=[CH:9][CH:8]=4)[CH:4]=3)=[O:15])[CH2:28]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 76257Diethyl cyanophosphonateHCID 516892Sodium BicarbonateHCID 10943925HCID 10943925, compoundHCID 21994001HCID 21994001, compound

Product 1

HCID 21993780HCID 21993780, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 0.406 g (1.860 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid, 0.62 g (2.05 mM) of 1-(3-phenylpropan-1-yl)piperidin-3-ylmethylamine dihydrochloride, and 1.04 ml (7.44 mM) of triethylamine in 10 ml of N,N-dimethylformamide was added 0.34 ml (2.23 mM) of diethyl cyanophosphate at room temperature and the mixture was stirred at the prevailing temperature overnight. This reaction mixture was poured in aqueous solution of sodium hydrogen carbonate and extracted with 3 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate-methanol=4/1 to 2/1) to provide the title compound.

Workup

  1. extractionextracted with 3 portions of ethyl acetate
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate-methanol=4/1 to 2/1)

Sources & evidence

ORD record
ord-5fa59d0b5ccb48768da8f40baec7068e
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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