Hydrogen Bromide → 1-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-3-ethylurea

HRID 1857601Notes

Reaction equation

HRID 1857601 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:36])=[C:27]([NH:30][C:31]([NH:33][CH2:34][CH3:35])=[O:32])[CH:28]=2)[NH:23][C:22](=[O:37])[C:21]=1[C:38]1[CH:43]=[C:42]([CH3:44])[CH:41]=[C:40]([CH3:45])[CH:39]=1)=O)C1C=CC=CC=1.Br>C(O)(=O)C>[Cl:36][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:38]3[CH:39]=[C:40]([CH3:45])[CH:41]=[C:42]([CH3:44])[CH:43]=3)[C:22](=[O:37])[NH:23]2)=[CH:28][C:27]=1[NH:30][C:31]([NH:33][CH2:34][CH3:35])=[O:32]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 538466182-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-(3-ethylureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 98920381-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-3-ethylurea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-(3-ethylureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester (50 mg in 5 mL of a 30% solution of hydrobromic acid in acetic acid) was stirred at room temperature for 18 hours then concentrated in vacuo. The residue was treated with saturated sodium bicarbonate and then extracted with methylene chloride. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 96:3:1) gave the title compound (18 mg). MASS: 497 (M+H)

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was treated with saturated sodium bicarbonate
  3. extractionextracted with methylene chloride
  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-26eb1a2f6d554767be3ead844a136e19
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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