3-Hydroxypyridine → HCID 21901945, compound

HRID 1593100Notes

Reaction equation

HRID 1593100 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-90bfef2d8e4d4faa890be9f78f095ff4
Source dataset
uspto-grants-2007_11
Patent number
US07294637B2

Reaction notes

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