Methanol → HCID 66620426, compound

HRID 415532Notes

Reaction equation

HRID 415532 reaction equation
[CH3:1][C:2]([CH3:27])([CH2:12][NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[N+:24]([O-])=O)[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].CO>[Pt].C1(C)C=CC=CC=1>[NH2:24][C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:14]=1[NH:13][CH2:12][C:2]([CH3:27])([CH3:1])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

5

Reactant 2

HCID 887MethanolHCID 66620044HCID 66620044, compound

Product 1

HCID 66620426HCID 66620426, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

A pressure bottle was charged with platinum on carbon (5%, 0.70 g) followed by tert-butyl 2,2-dimethyl-3-[(3-nitroquinolin-4-yl)amino]propylcarbamate dissolved in 250 mL of toluene. The reaction mixture was shaken under H2 at 48 PSI (3.3×105 Pa). The next day, the reaction mixture was carefully charged with 25 mL of MeOH and filtered through a pad of CELITE filter agent. The pad was rinsed with 1:1 CH2Cl2/methanol. The solvent was removed under reduced pressure to give tert-butyl 3-[(3-aminoquinolin-4-yl)amino]-2,2-dimethylpropylcarbamate as a light yellow solid.

Workup

  1. filtrationfiltered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with 1:1 CH2Cl2/methanol
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-096a065720ee4e5cb36e17218d54274a
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

Loading…