HCID 67500566, compound → Diethyl 1-(3-aminopyridin-4-yl)-4-chloropiperidin-3-ylphosphoramidate

HRID 1920203Notes

Reaction equation

HRID 1920203 reaction equation
[Cl:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:4][CH:3]1[NH:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>CCOC(C)=O.[Pd]>[NH2:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[N:5]1[CH2:6][CH2:7][CH:2]([Cl:1])[CH:3]([NH:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])[CH2:4]1

Participants

4

Reactant 1

HCID 67500566HCID 67500566, compound

Product 1

HCID 67500705Diethyl 1-(3-aminopyridin-4-yl)-4-chloropiperidin-3-ylphosphoramidateYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl 4-chloro-1-(3-nitropyridin-4-yl)piperidin-3-ylphosphoramidate (1.0 equiv.) in degassed EtOAc (0.1M) was added Pd/C (10% by weight) and the reaction was stirred under a hydrogen atmosphere for 18 h. Filtered and concentrated the filtrate to yield diethyl 1-(3-aminopyridin-4-yl)-4-chloropiperidin-3-ylphosphoramidate in 83% yield. LCMS (m/z): 363.1 (MH+), Rf=1.89 min.

Workup

  1. filtrationFiltered
  2. concentrationconcentrated the filtrate

Sources & evidence

ORD record
ord-8f6618330a914bfd808d42d1e7336065
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

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