3-Hydroxypyridine → HCID 72700245, compound

HRID 710611Notes

Reaction equation

HRID 710611 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[C:8](=[O:31])[C:9]3[CH:30]=[CH:29][CH:28]=[N:27][C:10]=3[N:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15](C#CC4C=NC=CC=4)[CH:14]=3)[N:12]=2)=[O:6])[CH2:3][CH2:2]1.[OH:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1.C(OC(C1CCCC1=O)=O)C.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.[Cu]I>[CH:1]1([NH:4][C:5]([C:7]2[C:8](=[O:31])[C:9]3[CH:30]=[CH:29][CH:28]=[N:27][C:10]=3[N:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:32][C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)[CH:14]=3)[N:12]=2)=[O:6])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 79713-HydroxypyridineHCID 10796Cesium carbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 72700164HCID 72700164, compound

Product 1

HCID 72700245HCID 72700245, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To N-cyclopropyl-4-oxo-1-[3-(pyridin-3-ylethynyl)phenyl]-1,4-dihydropyridino[2,3-c]pyridazine-3-formamide in 50 mL of DMSO was added in sequence 3-hydroxypyridine (0.48 g, 5 mmol), 2-oxocyclopentylcarboxylic acid ethyl ester (0.3 g, 2 mmol), CuI (0.4 g, 2 mmol), Cs2CO3 (2.6 g, 8 mmol), reacted in microwave reactor at 120° C. for 6 h. After reaction was complete, extraction was performed with H2O/DCM, and organic phase was separated to obtain product 26 mg.

Workup

  1. customreacted in microwave reactor at 120° C. for 6 h
  2. customAfter reaction
  3. extractionextraction
  4. customwas separated

Sources & evidence

ORD record
ord-ea9bb00c25524a18b4de8c8c594dc231
Source dataset
uspto-grants-2015_11
Patent number
US09181244B1

Reaction notes

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