Trifluoroacetic acid → 1-[3-(3-Bromophenyl)-7-chloro-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-3-cyclopropyl urea

HRID 1857619Notes

Reaction equation

HRID 1857619 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:34])=[C:24]([NH:27][C:28]([NH:30][CH:31]3[CH2:33][CH2:32]3)=[O:29])[CH:25]=2)[NH:20][C:19](=[O:35])[C:18]=1[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Br:42])[CH:37]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[Br:42][C:38]1[CH:37]=[C:36]([C:18]2[C:19](=[O:35])[NH:20][C:21]3[C:26]([C:17]=2[O:16][CH2:15][CH2:14][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]2)=[CH:25][C:24]([NH:27][C:28]([NH:30][CH:31]2[CH2:33][CH2:32]2)=[O:29])=[C:23]([Cl:34])[CH:22]=3)[CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 539044082-{2-[3-(3-Bromophenyl)-7-chloro-6-(3-cyclopropyl-ureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 221299931-[3-(3-Bromophenyl)-7-chloro-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-3-cyclopropyl ureaYield 50.5%

Reagents, catalysts & solvents 1

HCID 7519AnisoleCatalyst

Procedure

To a solution of 2-{2-[3-(3-bromophenyl)-7-chloro-6-(3-cyclopropyl-ureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (14 mg in 2.0 mL methylene chloride) was added 2 drops of anisole followed by 2.0 mL of trifluoroacetic acid and the mixture stirred at room temperature. After 30 minutes the solvents were removed in vacuo and the resulting residue purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 95:5:1; then 90:10:1) to give the title compound (6.0 mg).

Workup

  1. customAfter 30 minutes the solvents were removed in vacuo
  2. customthe resulting residue purified by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-ae46d8437b244060a09b22e0b0c47e02
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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