Dimethyl Sulfoxide → HCID 86646718, compound

HRID 1809111Notes

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.CS(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:35]1[N:40]=[CH:39][CH:38]=[CH:37][N:36]=1>CC#N>[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:19][CH2:20][N:21]([C:35]4[N:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:22][CH2:23]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

Participants

Conditions

Temperature: 180 °C

Procedure

cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (0.054 g, 0.16 mmol) was dissolved DMSO (1 mL) and cesium carbonate (0.5 mmol) was added followed by 2-chloropyrimidine (0.18 mmol). The reaction was heated to 180° C. by microwave irradiation for 45 minutes. The reaction mixture was diluted with MeCN (1 mL) and the mixture was filtered to remove any insoluble material. The filtrate was diluted with water and the mixture separated 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 as a pale yellow oil (0.015 g). LCMS m/z 411.25 [M+H]+ RT=12.36 min (Analytical Method 2).

Workup

additionwas added
filtrationthe mixture was filtered
customto remove any insoluble material
additionThe filtrate was diluted with water
customthe mixture separated 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-eec3e1b0c26046319ab95ec4e615c131
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362008B2

Reaction notes

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