Trifluoroacetic acid → 3-Chloro-N-cyclopentyl-N-(3-hydroxy-propyl)-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate

HRID 2268632Notes

Reaction equation

HRID 2268632 reaction equation
C(OC(=O)[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([C:23](=[O:34])[N:24]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:25][CH2:26][CH2:27][OH:28])[CH:20]=[C:19]([Cl:35])[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(C)(C)C.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>ClCCl>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[Cl:35][C:19]1[CH:20]=[C:21]([CH:22]=[C:17]([O:16][CH2:15][CH2:14][NH:7][C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)[CH:18]=1)[C:23]([N:24]([CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33]1)[CH2:25][CH2:26][CH2:27][OH:28])=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54299674(2-{3-Chloro-5-[cyclopentyl-(3-hydroxy-propyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester

Product 1

HCID 183492073-Chloro-N-cyclopentyl-N-(3-hydroxy-propyl)-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-{3-chloro-5-[cyclopentyl-(3-hydroxy-propyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tertbutyl ester (0.07 g) in a mixture of dichloromethane (2 ml) and trifluoroacetic acid (2 ml) was stored at room temperature for 1 h and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.011 g) was obtained as a colourless gum by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f09d7994ffb4dd6ac239e894e655839
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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