2-Bromoethanol → HCID 68792870, compound

HRID 1809073Notes

Reaction equation

[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[C:24](=O)([O-:26])[O-:25].[K+].[K+].Br[CH2:31][CH2:32][OH:33]>CC#N>[CH:24]([O-:26])=[O:25].[OH:33][CH2:32][CH2:31][N@H+:21]1[CH2:20][CH2:19][C@@H:18]([C:16]2[S:15][CH:14]=[C:13]([C:11]([N:1]3[CH:10]4[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]4)[CH2:4][CH2:3][CH2:2]3)=[O:12])[CH:17]=2)[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 60 °C

Procedure

cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (0.029 g, 0.087 mmol) was dissolved MeCN (1 mL) and potassium carbonate (36 mmol) was added followed by 2-bromoethanol (22 mg). The reaction was heated to 60° C. and stirred for 5 hours. The product was purified by flash chromatography on a SCX-2 cartridge, eluting with acetonitrile and then 2 M ammonia in methanol. The residue was further purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound (0.046 g). LCMS m/z 377.17 min [M+H]+ RT=6.45 min (Analytical Method 2).

Workup

additionwas added
customThe product was purified by flash chromatography on a SCX-2 cartridge
washeluting with acetonitrile
customThe residue was further purified by HPLC
washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
additionThe fractions containing the desired product
concentrationwere concentrated under vacuum

Sources & evidence

ORD record: ord-1c2a930d77c34d2885844151ab70e097
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362008B2

Reaction notes

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