{2-[(6-Nitro-1H-indole-2-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester → {2-[(6-Amino-1H-indole-2-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester

HRID 724518Notes

Reaction equation

HRID 724518 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([N+:22]([O-])=O)[CH:16]=2)=[O:12])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([NH2:22])[CH:16]=2)=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58747124{2-[(6-Nitro-1H-indole-2-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 69528719{2-[(6-Amino-1H-indole-2-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 35 (0.184 g, 0.528 mmol) was dissolved in 15 ml of MeOH and hydrogenated over 5% Pd/C under 40 psi of H2 for 30 min. TLC showed that reaction was completed. After filtration through celite, the filtrate was evaporated and the residue was dried under high vacuum to give compound 36.

Workup

  1. customTLC showed that reaction
  2. filtrationAfter filtration through celite
  3. customthe filtrate was evaporated
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-9db8c0b5eec342eeab7c6a3b1f10107f
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

Loading…