HCID 68011950, compound → HCID 67503907, compound

HRID 868803Notes

Reaction equation

HRID 868803 reaction equation
[CH2:1]([NH:8][C:9](=[O:41])[C@@H:10]([NH:25][C:26]([C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([N:38]([CH3:40])[CH3:39])[CH:34]=2)[CH:29]=1)=[O:27])[CH2:11][CH2:12][CH2:13][NH:14]C(=O)OCC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[NH2:14][CH2:13][CH2:12][CH2:11][C@H:10]([NH:25][C:26]([C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([N:38]([CH3:40])[CH3:39])[CH:34]=2)[CH:29]=1)=[O:27])[C:9]([NH:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:41]

Participants

4

Reactant 1

HCID 68011950HCID 68011950, compound

Product 1

HCID 67503907HCID 67503907, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the solution of (S)-benzyl 5-(benzylamino)-4-(6-(dimethylamino)-2-naphthamido)-5-oxopentylcarbamate (80 mg, 0.145 mmol) in methanol (10 ml) of was added Pd/C (10%) 10 mg. The reaction mixture was stirred under H2 balloon for 8 hr at rt. After filtration the filtrate was evaporated in vacuo and the residue was triturated with ether repeatedly to provide (S)—N-(5-amino-1-(benzylamino)-1-oxopentan-2-yl)-6-(dimethylamino)-2-naphthamide as colorless powder.

Workup

  1. filtrationAfter filtration the filtrate
  2. customwas evaporated in vacuo
  3. customthe residue was triturated with ether repeatedly

Sources & evidence

ORD record
ord-f6084220f966412d8dacfdce4887e292
Source dataset
uspto-grants-2015_03
Patent number
US08969333B2

Reaction notes

Loading…