HCID 86619533, compound → HCID 86619535, compound

HRID 1663433Notes

Reaction equation

HRID 1663433 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=[CH:25][C:24]=1[N+:33]([O-])=O)[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(#N)C.[Pt]>[NH2:33][C:24]1[CH:25]=[N:26][C:27]2[C:32]([C:23]=1[NH:22][C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:31][CH:30]=[CH:29][CH:28]=2

Participants

4

Reactant 1

HCID 86619533HCID 86619533, compound

Product 1

HCID 86619535HCID 86619535, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl (4S)-5-{[tert-butyl(dimethyl)silyl]oxy}-4-[(3-nitroquinolin-4-yl)amino]pentylcarbamate (5.65 g, 11.2 mmol) was dissolved in 100 mL of acetonitrile and the solution was placed in a pressure bottle. Platinum on carbon (5%, 1.2 g) was then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 4 hours, an additional 500 mg of platinum on carbon was added and shaking was continued for 3 hours. The reaction mixture was then filtered through a pad of CELITE filter agent. The pad was rinsed with acetonitrile and the combined filtrates were concentrated under reduced pressure to give tert-butyl (4S)-4-[(3-aminoquinolin-4-yl)amino]-5-{[tert-butyl(dimethyl)silyl]oxy}pentylcarbamate (4.61 g) as an orange foam.

Workup

  1. stirringshaking
  2. waitwas continued for 3 hours
  3. filtrationThe reaction mixture was then filtered through a pad of CELITE
  4. filtrationfilter agent
  5. washThe pad was rinsed with acetonitrile
  6. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-e4c818ff07cc46d6ae4db46793f0a89b
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

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