HCID 66958437, compound → HCID 66958490, compound

HRID 1364017Notes

Reaction equation

HRID 1364017 reaction equation
[Si:1]([O:8][CH:9]([CH2:19][NH:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][C:22]=1[N+:31]([O-])=O)[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>ClCCl>[NH2:31][C:22]1[CH:23]=[N:24][C:25]2[C:30]([C:21]=1[NH:20][CH2:19][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[CH:29][CH:28]=[CH:27][CH:26]=2

Participants

3

Reactant 1

HCID 66958437HCID 66958437, compound

Product 1

HCID 66958490HCID 66958490, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-{[tert-butyl(dimethyl)silyl]oxy}-3-[(3-nitroquinolin-4-yl)amino]propylcarbamate (110.18 g, 231.16 mmol) in dichloromethane (500 mL) was added to a Parr vessel. The system was purged with nitrogen, and 10% palladium on carbon (14.76 g, 138.7 mnmol) was added. The vessel was placed under hydrogen pressure (30 psi, 2.1×105 Pa) and shaken for four hours. The reaction mixture was filtered, and, the filtrate was passed through a plug of silica gel and concentrated under reduced pressure to provide 103.45 g of tert-butyl 3-[(3-aminoquinolin-4-yl)amino]-2-{[tert-butyl(dimethyl)silyl]oxy}propylcarbamate.

Workup

  1. customThe system was purged with nitrogen, and 10% palladium on carbon (14.76 g, 138.7 mnmol)
  2. additionwas added
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-762e616e6efb444da76331636d245c38
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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