Water → N-(2-Carbamoyl-ethyl)-3-chloro-N-cyclobutyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate

HRID 2268685Notes

Reaction equation

HRID 2268685 reaction equation
C(OC(=O)[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([C:23](=[O:33])[N:24]([CH2:29][CH2:30][C:31]#[N:32])[CH:25]2[CH2:28][CH2:27][CH2:26]2)[CH:20]=[C:19]([Cl:34])[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(C)(C)C.[OH2:36].[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].[C:31]([CH2:30][CH2:29][N:24]([CH:25]1[CH2:28][CH2:27][CH2:26]1)[C:23](=[O:33])[C:21]1[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]=[C:19]([Cl:34])[CH:20]=1)(=[O:36])[NH2:32]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 54411432(2-{3-Chloro-5-[(2-cyano-ethyl)-cyclobutyl-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester

Product 1

HCID 18349117N-(2-Carbamoyl-ethyl)-3-chloro-N-cyclobutyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-{3-chloro-5-[(2-cyano-ethyl)-cyclobutyl-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester (0.042 g) and water (0.050 ml) in mixture of trifluoroacetic acid (1 ml) and dichloromethane (1 ml) was stored at room temperature for 24 h and then the solvent removed under reduced pressure. The residue was subjected to preparative hplc to give the title compound (0.027 g) 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. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-534ea23a888a4bc0945f56d83c6621a5
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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