HCID 86656454, compound → HCID 86656453, compound

HRID 1028055Notes

Reaction equation

HRID 1028055 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][N:17]=2)[N:14]=[CH:13][CH:12]=[C:11]3[N:18]2[CH2:23][CH2:22][CH2:21][C@H:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:19]2)[C:5]([N+:32]([O-])=O)=[CH:4][CH:3]=1>C(O)(=O)C.[Fe]>[NH2:32][C:5]1[C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][N:17]=2)[N:14]=[CH:13][CH:12]=[C:11]3[N:18]2[CH2:23][CH2:22][CH2:21][C@H:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH2:19]2)=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 86656454HCID 86656454, compound

Product 1

HCID 86656453HCID 86656453, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A heterogeneous solution of (S)-tert-butyl 1-(6-(6-chloro-3-nitropyridin-2-yl)-1,7-naphthyridin-4-yl)piperidin-3-ylcarbamate (1.0 eq.) and iron (6.0 eq) in acetic acid, at a concentration of 0.4 M, was stirred vigorously for 14 hours. The mixture was then passed through a celite pad, eluting with MeOH. Upon removal of the volatiles in vacuo, the residue was dissolved in EtOAc, washed with Na2CO3(sat.), NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding (S)-tert-butyl 1-(6-(3-amino-6-chloropyridin-2-yl)-1,7-naphthyridin-4-yl)piperidin-3-ylcarbamate (77%). LCMS (m/z): 455.2 (MH+); LC Rt=3.10 min.

Workup

  1. washeluting with MeOH
  2. customUpon removal of the volatiles in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with Na2CO3(sat.), NaCl(sat.)
  5. dry with materialwas dried over MgSO4
  6. filtrationwas filtered
  7. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-cf0df91d0f3c4796bd0d8005c03c28bc
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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