Trifluoroacetic acid → 1-[7-Chloro-2-oxo-4-(2-piperidin-2-yl-ethoxy)-3-thiophen-2-yl-1,2-dihydroquinolin-6-yl]-3-pyridin-4-yl-urea

HRID 1858169Notes

Reaction equation

HRID 1858169 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:37])=[C:24]([NH:27][C:28]([NH:30][C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)=[O:29])[CH:25]=2)[NH:20][C:19](=[O:38])[C:18]=1[C:39]1[S:40][CH:41]=[CH:42][CH:43]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:37][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([O:16][CH2:15][CH2:14][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[C:18]([C:39]3[S:40][CH:41]=[CH:42][CH:43]=3)[C:19](=[O:38])[NH:20]2)=[CH:25][C:24]=1[NH:27][C:28]([NH:30][C:31]1[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=1)=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 539673912-{2-[7-Chloro-2-oxo-6-(3-pyridin-4-yl-ureido)-3-thiophen-2-yl-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 98496751-[7-Chloro-2-oxo-4-(2-piperidin-2-yl-ethoxy)-3-thiophen-2-yl-1,2-dihydroquinolin-6-yl]-3-pyridin-4-yl-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{2-[7-chloro-2-oxo-6-(3-pyridin-4-yl-ureido)-3-thiophen-2-yl-1,2-dihydroquinolin-4-yloxy]-ethyl }-piperidine-1-carboxylic acid tert-butyl ester in methylene chloride is added trifluoroacetic acid and the mixture stirred at room temperature. After 30 minutes, the mixture is concentrated in vacuo, resolvated in 10% ammonium hydroxide in methanol and concentrated once again. Purification by flash chromatography on silica gel gives the title compound.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. concentrationconcentrated once again
  3. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-496efc17784e42e4a1bcfdcaae4297e6
Source dataset
uspto-grants-2000_11
Patent number
US06150522

Reaction notes

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