Trifluoroacetic acid → N-Allyl-3-chloro-N-cyclopentyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate salt

HRID 2268630Notes

Reaction equation

HRID 2268630 reaction equation
C(OC(=O)[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([C:24](=[O:35])[N:25]([CH2:32][CH:33]=[CH2:34])[CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28]C2)[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].[CH2:32]([N:25]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:24](=[O:35])[C:19]1[CH:18]=[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:22]=[C:21]([Cl:23])[CH:20]=1)[CH:33]=[CH2:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53724634{2-[3-(Allyl-cyclohexyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester

Product 1

HCID 18349184N-Allyl-3-chloro-N-cyclopentyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {2-[3-(allyl-cyclohexyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester (0.032 g) in a mixture of dichloromethane (1 ml) and trifluoroacetic acid (1 ml) was stored at room temperature for 2 h and then concentrated under reduced pressure. The residue was subjected to preparative hplc and the title compound (0.027 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-9bad994383f54b56bdc386bd148330c2
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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