Cesium carbonate → HCID 131731012, compound

HRID 2035605Notes

Reaction equation

[F:1][C@H:2]1[C@H:7]([O:8]S(C)(=O)=O)[CH2:6][CH2:5][N:4]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:3]1.[F:20][C:21]1[CH:22]=[CH:23][C:24]2[N:25]([C:27]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[C:33](O)[CH:34]=[CH:35][CH:36]=4)[N:31]=3)=[N:28][N:29]=2)[CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(N(C)C)=O>CCOC(C)=O.O>[F:1][C@H:2]1[C@@H:7]([O:8][C:33]2[CH:34]=[CH:35][CH:36]=[C:37]3[C:32]=2[N:31]=[C:30]([C:27]2[N:25]4[CH:26]=[C:21]([F:20])[CH:22]=[CH:23][C:24]4=[N:29][N:28]=2)[CH:39]=[CH:38]3)[CH2:6][CH2:5][N:4]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (trans)-tert-butyl 3-fluoro-4-(methylsulfonyloxy)piperidine-1-carboxylate (24 mg, 0.0807 mmol), 2-(6-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol (23.8 mg, 0.0850 mmol) and Cs2CO3 (55.4 mg, 0.170 mmol) in DMA (425 μl, 0.0850 mmol) was heated to 90° C. for 16 hours. The mixture was transferred to a reparatory funnel and diluted with EtOAc and water. The mixture was then extracted with EtOAc, and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to a residue under reduced pressure to give the product without further purification (33 mg, 81% yield). MS APCI (+) m/z 481.9 (M+1) detected.

Workup

customThe mixture was transferred to a reparatory funnel
extractionThe mixture was then extracted with EtOAc
washthe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to a residue under reduced pressure
customto give the product
customwithout further purification (33 mg, 81% yield)

Sources & evidence

ORD record: ord-6770fd0a05f64eb0abd31fcdf87716a2
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575145B2

Reaction notes

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