Dimethylformamide → 1-(8-Fluoroquinolin-4-yl)-3-(6-(tetrahydro-2H-pyran-4-yl)pyridin-2-yl)urea

HRID 1528095Notes

Reaction equation

HRID 1528095 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]([NH:16][C:17]3[C:26]4[C:21](=[C:22]([F:27])[CH:23]=[CH:24][CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[O:15])[CH:10]=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.CN(C=O)C.[H][H]>[Pd].CO.CC(O)=O>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:21]=1[N:20]=[CH:19][CH:18]=[C:17]2[NH:16][C:14]([NH:13][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[N:12]=1)=[O:15]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 575212631-(6-(3,6-Dihydro-2H-pyran-4-yl)pyridin-2-yl)-3-(8-fluoroquinolin-4-yl)ureaHCID 178418361HCID 178418361, compound

Product 1

HCID 574095721-(8-Fluoroquinolin-4-yl)-3-(6-(tetrahydro-2H-pyran-4-yl)pyridin-2-yl)ureaYield 99%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (1-(6-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yl)-3-(8-fluoroquinolin-4-yl)urea (21 mg, 0.058 mmol) and 12.3 mg of palladium on charcoal in 20 mL of methanol together with 1 mL of DMF and 1 drop of AcOH was stirred under 1 atm of hydrogen for 18 h. Filtration and evaporation to dryness afforded 21 mg (99%) of the desired title product.

Workup

  1. filtrationFiltration and evaporation to dryness

Sources & evidence

ORD record
ord-fa27df3eeb1d4bccb7912313bf3cc08f
Source dataset
uspto-grants-2015_07
Patent number
US09090592B2

Reaction notes

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