Trifluoroacetic acid → 3-Chloro-N-isopropyl-N-[2-(1-methyl-1H-tetrazol-5-yl)-ethyl]-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate

HRID 2268658Notes

Reaction equation

HRID 2268658 reaction equation
C(OC(=O)[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([C:23](=[O:36])[N:24]([CH:33]([CH3:35])[CH3:34])[CH2:25][CH2:26][C:27]2[N:31]([CH3:32])[N:30]=[N:29][N:28]=2)[CH:20]=[C:19]([Cl:37])[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(C)(C)C.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[Cl:37][C:19]1[CH:20]=[C:21]([CH:22]=[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:18]=1)[C:23]([N:24]([CH:33]([CH3:35])[CH3:34])[CH2:25][CH2:26][C:27]1[N:31]([CH3:32])[N:30]=[N:29][N:28]=1)=[O:36]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54506817[2-(3-Chloro-5-{isopropyl-[2-(1-methyl-1H-tetrazol-5-yl)-ethyl]-carbamoyl}-phenoxy)-ethyl]-pyridin-4-yl-carbamic acid tert-butyl ester

Product 1

HCID 183490463-Chloro-N-isopropyl-N-[2-(1-methyl-1H-tetrazol-5-yl)-ethyl]-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate

Procedure

A solution of [2-(3-chloro-5-{isopropyl-[2-(1-methyl-1H-tetrazol-5-yl)-ethyl]-carbamoyl}phenoxy)-ethyl]-pyridin-4-yl-carbamic acid tert-butyl ester (0.028 g) in a mixture of dichtoromethane (0.5 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 (0.023 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-ce916db77897499d9b607eff0140e4e5
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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