Hydrogen Bromide → HCID 68493794, compound

HRID 1966513Notes

Reaction equation

HRID 1966513 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[Cl:37])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[C:12]([N:17]3[CH2:22][CH2:21][N:20](S(C4C=CC(C)=CC=4)(=O)=O)[CH2:19][CH2:18]3)[CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([CH3:33])[CH:8]=1.Br>O>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[Cl:37])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[C:12]([N:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)[CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([CH3:33])[CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 25217467HCID 25217467, compound

Product 1

HCID 68493794HCID 68493794, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

(3,4-Dichlorobenzyl)-{2-methyl-8-[4-(toluene-4-sulfonyl)-piperazin-1-yl]-quinolin-4-yl}-amine (example 17, 40 mg, 0.072 mmole) and a mixture of HBr/glacial acetic acid (33%, 1 mL)/0.2 mL) were stirred at 70° C. for 3 hrs. The content of the flask was diluted with water and extracted with ethyl acetate. The aqueous phase was alkalized and extracted with dichloromethane. The organic phases were washed with saturated NaCl solution and concentrated. The residue was crystallized as hydrochloride from isopropanol/iso-propyl ether/ethanol/HCl to give a light fawn salt (17 mg, 50%).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with dichloromethane
  3. washThe organic phases were washed with saturated NaCl solution
  4. concentrationconcentrated
  5. customThe residue was crystallized as hydrochloride from isopropanol/iso-propyl ether/ethanol/HCl

Sources & evidence

ORD record
ord-1280d39e317d4b56b0c2acff04ec9aa3
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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