(S)-2-(5-(diethylamino)-2-nitrophenyl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isonicotinamide → HCID 66586895, compound

HRID 625437Notes

Reaction equation

HRID 625437 reaction equation
[CH2:1]([N:3]([CH2:32][CH3:33])[C:4]1[CH:5]=[CH:6][C:7]([N+:29]([O-])=O)=[C:8]([C:10]2[CH:11]=[C:12]([CH:26]=[CH:27][N:28]=2)[C:13]([NH:15][C@@H:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH2:17]2)=[O:14])[CH:9]=1)[CH3:2]>CO.[Pd]>[NH2:29][C:7]1[CH:6]=[CH:5][C:4]([N:3]([CH2:32][CH3:33])[CH2:1][CH3:2])=[CH:9][C:8]=1[C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][N:28]=1)[C:13]([NH:15][C@@H:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1)=[O:14]

Participants

4

Reactant 1

HCID 66587605(S)-2-(5-(diethylamino)-2-nitrophenyl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isonicotinamide

Product 1

HCID 66586895HCID 66586895, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-2-(5-(diethylamino)-2-nitrophenyl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isonicotinamide (4.73 g) and 10% Pd/C (1.3 g) in methanol (20 mL) was stirred under a hydrogen atmosphere for 2 h. The mixture was filtered and concentrated to give a brown solid (4 g, 91%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a43ff94c166c43d08255c96e14e18728
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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