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

HRID 2268629Notes

Reaction equation

HRID 2268629 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:34])[N:25]([CH2:31][CH:32]=[CH2:33])[CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(C)(C)C.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>ClCCl>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[CH2:31]([N:25]([CH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[C:24](=[O:34])[C:19]1[CH:18]=[C:17]([O:16][CH2:15][CH2:14][NH:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:22]=[C:21]([Cl:23])[CH:20]=1)[CH:32]=[CH2:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18349220{2-[3-(Allyl-cyclopentyl-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-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester (0.030 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 (0.026 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 The residue

Sources & evidence

ORD record
ord-e0b51ec04fc94fc8a1300ced7ea81379
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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