4-Aminopyridine → HCID 58002311, compound

HRID 1643133Notes

Reaction equation

HRID 1643133 reaction equation
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH2:43]([C:45]1[CH:50]=[CH:49][C:48]([CH:51]2[CH2:56][N:55]([C:57]([N:59]3[CH2:64][CH2:63][O:62][CH2:61][CH2:60]3)=[O:58])[CH2:54][CH:53]([C:65]3[S:66][CH:67]=[C:68]([C:70]([OH:72])=O)[N:69]=3)[CH2:52]2)=[CH:47][CH:46]=1)[CH3:44].[NH2:73][C:74]1[CH:79]=[CH:78][N:77]=[CH:76][CH:75]=1>C1COCC1>[CH2:43]([C:45]1[CH:50]=[CH:49][C:48]([CH:51]2[CH2:56][N:55]([C:57]([N:59]3[CH2:60][CH2:61][O:62][CH2:63][CH2:64]3)=[O:58])[CH2:54][CH:53]([C:65]3[S:66][CH:67]=[C:68]([C:70]([NH:73][C:74]4[CH:79]=[CH:78][N:77]=[CH:76][CH:75]=4)=[O:72])[N:69]=3)[CH2:52]2)=[CH:47][CH:46]=1)[CH3:44]

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58002380HCID 58002380, compound

Product 1

HCID 58002311HCID 58002311, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

145 mg (0.279 mmol) of PYBOP and 169 mg (1.304 mmol) of N,N-diisopropylethylamine were added to a mixture of 80 mg (0.186 mmol) of the compound from Example 143A in 0.5 ml of THF. The reaction mixture was stirred at room temperature for 40 minutes. 21 mg (0.223 mmol) of 4-aminopyridine were then added, and stirring of the mixture at RT was continued overnight. For work-up, the solvent was evaporated and the residue was taken up in ethyl acetate. The organic phase was washed successively with water and saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. Diastereomer separation of the cis/trans isomer mixture according to Method 12C gave 14 mg of the title compound (cis isomer) and 23 mg of the trans isomer.

Workup

  1. stirringstirring of the mixture at RT
  2. waitwas continued overnight
  3. customFor work-up, the solvent was evaporated
  4. washThe organic phase was washed successively with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customDiastereomer separation of the cis/trans isomer mixture

Sources & evidence

ORD record
ord-06941414e76a41e9a33fa65324efe5b2
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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