Diethyl cyanophosphonate → HCID 70248359, compound

HRID 1978417Notes

Reaction equation

HRID 1978417 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]([CH:13]=[CH:14][C:15]([OH:17])=O)=[CH:4]2.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][NH2:32])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].P(C#N)(OCC)(OCC)=O.C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)CC)C>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][NH:32][C:15](=[O:17])[CH:14]=[CH:13][C:5]2[S:6][C:7]3[N:12]4[C:3](=[CH:2][N:1]=[C:11]4[CH:10]=[CH:9][CH:8]=3)[CH:4]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 76257Diethyl cyanophosphonateHCID 516892Sodium BicarbonateHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 53673182HCID 53673182, compound

Product 1

HCID 70248359HCID 70248359, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

While 0.708 g (2.898 mM) of 3-(5-thia-1,8b-diazaacenaphthylen-4-yl)acrylic acid, 0.68 g (3.19 mM) of 1-(tert-butoxycarbonyl)piperidin-4-ylmethylamine, and 0.48 ml (3.48 mM) of triethylamine were stirred together in 10 ml of N,N-dimethylformamide, 0.53 ml (3.48 mM) of diethyl cyanophosphate was added dropwise 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 subjected to silica gel column chromatography (ethyl acetate to ethyl acetate-methanol=9/1) to provide crude N-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-3-(5-thia-1,8b-diazaacenaphthylen-4-yl)acrylamide.

Workup

  1. extractionextracted with 3 portions of ethyl acetate
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2451e341d81d486ab078c134dc563ae7
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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