Isopropanol → HCID 66957881, compound

HRID 9433Notes

Reaction equation

HRID 9433 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([Br:21])=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:22]([O-])=O)([CH3:4])([CH3:3])[CH3:2].C(O)(C)C>C(#N)C.[Pt]>[NH2:22][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:11]=1[NH:10][CH2:9][CH2:8][NH:7][C:6](=[O:25])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=2

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 21984156Tert-butyl[2-(7-bromo-3-nitroquinolin-4-ylamino)ethyl]carbamate

Product 1

HCID 66957881HCID 66957881, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl[2-(7-bromo-3-nitroquinolin-4-ylamino)ethyl]carbamate (165.0 g, 401.2 mmol) in acetonitrile (3.3 L) and, isopropanol (990 mL) and 5% platinum on carbon (13.2 g) were added to a Parr vessel, which was placed under hydrogen pressure (50 psi, 3.4×105 Pa) overnight. The mixture was filtered through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure to provide 139.29 g of tert-butyl [2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]carbamate as a yellow solid. The product was suspended in a mixture of dichloromethane (4 mL/g) and chloroform (8 mL/g), and the suspension was divided into two equal portions.

Workup

  1. custompressure (50 psi, 3.4×105 Pa) overnight
  2. filtrationThe mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4c81e4ee6509425ba1349d592b141c5f
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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