Hydrogen Bromide → 1-[7-Chloro-3-(3,5-dimethyl-phenyl)-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydro-quinolin-6-yl]-3-pyridin-4-yl-urea

HRID 1858067Notes

Reaction equation

HRID 1858067 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:40])=[C:27]([NH:30][C:31]([NH:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)=[O:32])[CH:28]=2)[NH:23][C:22](=[O:41])[C:21]=1[C:42]1[CH:47]=[C:46]([CH3:48])[CH:45]=[C:44]([CH3:49])[CH:43]=1)=O)C1C=CC=CC=1.Br>C(O)(=O)C>[Cl:40][C:26]1[CH:25]=[C:24]2[C:29]([C:20]([O:19][CH2:18][CH2:17][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][NH:11]3)=[C:21]([C:42]3[CH:47]=[C:46]([CH3:48])[CH:45]=[C:44]([CH3:49])[CH:43]=3)[C:22](=[O:41])[NH:23]2)=[CH:28][C:27]=1[NH:30][C:31]([NH:33][C:34]1[CH:35]=[CH:36][N:37]=[CH:38][CH:39]=1)=[O:32]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 543905802-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-pyridin-4-yl-ureido)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 99591211-[7-Chloro-3-(3,5-dimethyl-phenyl)-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydro-quinolin-6-yl]-3-pyridin-4-yl-urea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-pyridin-4-yl-ureido)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester in 3 mL of a 30% solution of hydrobromic acid in acetic acid was stirred at room temperature for 3 hours then concentrated in vacuo. The residue was treated with saturated sodium bicarbonate and then extracted with ethyl acetate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 96:3:1) gave the title compound.

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was treated with saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. customPurification of the
  5. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 96:3:1)

Sources & evidence

ORD record
ord-5dde6b86068d4991a69c9914d8770feb
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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