HCID 86619537, compound → HCID 86619539, compound

HRID 1803386Notes

Reaction equation

HRID 1803386 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C@@H:7]([NH:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][C:21]=1[N+:30]([O-])=O)[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:4])=[O:3]>C(#N)C.[Pt]>[NH2:30][C:21]1[CH:22]=[N:23][C:24]2[C:29]([C:20]=1[NH:19][C@H:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[CH:28][CH:27]=[CH:26][CH:25]=2

Participants

4

Reactant 1

HCID 86619537HCID 86619537, compound

Product 1

HCID 86619539HCID 86619539, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

tert-Butyl (4S)-5-[(methylsulfonyl)amino]-4-[(3-nitroquinolin-4-yl)amino]pentylcarbamate (8.00 g, 17.1 mmol) was dissolved in 150 mL of acetonitrile and the solution was placed in a pressure bottle. Platinum on carbon (5%, 2.0 g) was then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 2 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-[(methylsulfonyl)amino]pentylcarbamate (7.13 g) as an orange foam.

Workup

  1. filtrationthe reaction mixture was then filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with acetonitrile
  4. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ca5cd18f5a74889a6575f66283fd6b1
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

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