3-Hydroxypyridine → HCID 21901945, compound

HRID 1160347Notes

Reaction equation

HRID 1160347 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([C:25]([N:27]3[CH2:32][CH2:31][CH2:30][CH:29]([CH2:33]OS(C)(=O)=O)[CH2:28]3)=[O:26])[CH2:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.O1C2C=CC(OCC3CCCN(C(C4(C5C=CC(Cl)=CC=5)CCC4)=O)C3)=CC=2OC1>>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([C:25]([N:27]3[CH2:32][CH2:31][CH2:30][CH:29]([CH2:33][O:1][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=4)[CH2:28]3)=[O:26])[CH2:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 79713-HydroxypyridineHCID 10796Cesium carbonateHCID 12992442Methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl esterHCID 21902076HCID 21902076, compound

Product 1

HCID 21901945HCID 21901945, compoundYield 52%

Procedure

Compound 85 was synthesized from 3-hydroxypyridine (0.25 g, 2.60 mmol), cesium carbonate (1.27 g, 3.89 mmol) and compound 43 (1.0 g, 2.60 mmol), using the method described for the synthesis of compound 44 to give 0.52 g of the desired product 85. C22H25ClN2O2, LRMS (m/z)=385 MH+).

Sources & evidence

ORD record
ord-2f163ae9e7374e0c996eca0a838678c6
Source dataset
uspto-grants-2010_10
Patent number
US07816375B2

Reaction notes

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