Ethanolamine → HCID 131724837, compound

HRID 1593812Notes

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].[Cl:5][C:6]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28]OS(C)(=O)=O)=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:9]>C(O)CCC.C(OCC)(=O)C>[C:1]([OH:9])(=[O:2])[CH3:3].[Cl:5][C:6]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][NH:4][CH2:3][CH2:1][OH:2])=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethanolamine (0.07 ml) was added to a suspension of 2-chloro-5-[3-[(methylsulfonyl)oxy]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 6e, 0.170 g) in n-butanol (5 ml) and heated at 100° C. in a sealed tube for 12 h. On cooling to ambient temperature the solution was diluted with ethyl acetate and extracted twice with saturated aqueous sodium hydrogencarbonate solution and once with brine, dried over magnesium sulfate and concentrated under reduced pressure. Purification by preperative reverse phase HPLC (eluting with a gradient of acetonitrile in 0.1% aqueous ammonium acetate/25-95%) gave the title compound as the acetate salt (0.070 g).

Workup

temperatureOn cooling to ambient temperature the solution
extractionextracted twice with saturated aqueous sodium hydrogencarbonate solution and once with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customPurification by preperative reverse phase HPLC (
washeluting with a gradient of acetonitrile in 0.1% aqueous ammonium acetate/25-95%)

Sources & evidence

ORD record: ord-df4e2bcd358e4b9aa7071b0cd5bfba9f
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07297818B2

Reaction notes

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