2-[4-(1-Azido-1-methylethyl)phenyl]-5-methoxy-3-(2-thienyl)-1,6-naphthyridine → 2-{4-[5-Methoxy-3-(2-thienyl)-1,6-naphthyridin-2-yl]phenyl}propan-2-amine

HRID 732874Notes

Reaction equation

HRID 732874 reaction equation
[N:1]([C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:22]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[N:18][C:19]=3[O:28][CH3:29])[N:14]=2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5])=[N+]=[N-].[H][H]>CCO.[Pd]>[CH3:29][O:28][C:19]1[N:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[CH:21]=[C:22]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[C:13]([C:10]1[CH:9]=[CH:8][C:7]([C:4]([NH2:1])([CH3:6])[CH3:5])=[CH:12][CH:11]=1)=[N:14]2

Participants

5

Reactant 2

HCID 866174642-[4-(1-Azido-1-methylethyl)phenyl]-5-methoxy-3-(2-thienyl)-1,6-naphthyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 690592742-{4-[5-Methoxy-3-(2-thienyl)-1,6-naphthyridin-2-yl]phenyl}propan-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-[4-(1-azido-1-methylethyl)phenyl]-5-methoxy-3-(2-thienyl)-1,6-naphthyridine (2-5, 78 mg, 0.194 mmol) and 10% Pd/C (9 mg) was stirred under 1atm hydrogen in EtOH (5 mL) for 2 h. The mixture was filtered through celite and concentrated to give the title compound as a clear oil. LRMS m/z (M+1) Calcd: 376.1,. Found 376.2.

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c228d940fb794cf1abf1648cb761108b
Source dataset
uspto-grants-2009_09
Patent number
US07589068B2

Reaction notes

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