Propionamide → HCID 71575877, compound

HRID 1411160Notes

Reaction equation

HRID 1411160 reaction equation
[Cl:1][C:2]1[C:3]([O:29][C:30]2[CH:35]=[CH:34][N:33]=[C:32](Cl)[CH:31]=2)=[CH:4][C:5]([F:28])=[C:6]([NH:8][C:9]([C:11]2[C:12](=[O:27])[N:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:14]=[CH:15][C:16]=2[O:17][CH2:18][CH3:19])=[O:10])[CH:7]=1.[C:37]([NH2:41])(=[O:40])[CH2:38][CH3:39].C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:1][C:2]1[C:3]([O:29][C:30]2[CH:35]=[CH:34][N:33]=[C:32]([NH:41][C:37](=[O:40])[CH2:38][CH3:39])[CH:31]=2)=[CH:4][C:5]([F:28])=[C:6]([NH:8][C:9]([C:11]2[C:12](=[O:27])[N:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:14]=[CH:15][C:16]=2[O:17][CH2:18][CH3:19])=[O:10])[CH:7]=1

Participants

7

Reactant 4

HCID 6578PropionamideHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86703366HCID 86703366, compound

Product 1

HCID 71575877HCID 71575877, compoundYield 16.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the procedure of Example 12, N-(5-chloro-4-((2-chloropyridin-4-yl)oxy)-2-fluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (0.05 g, 0.094 mmol), propionamide (10 mg, 0.14 mmol), Cs2CO3 (0.05 g, 0.14 mmol), Xantphos (6 mg, 0.010 mmol), Pd2(dba)3 (5 mg, 0.005 mmol) and dioxane (2 mL) were combined to obtain N-(5-chloro-2-fluoro-4-((2-propionamidopyridin-4-yl)oxy)phenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (9 mg, 16% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.16 (s, 1H), 10.46 (s, 1H), 8.46 (d, J=7.8 Hz, 1H), 8.13 (d, J=5.7 Hz, 1H), 7.87 (d, J=7.8 Hz, 1H), 7.57 (d, J=2.4 Hz, 1H), 7.45 (m, 3H), 7.31 (t, J=8.7 Hz, 2H), 6.62 (dd, J=5.7, 2.4 Hz, 1H), 6.50 (d, J=7.9 Hz, 1H), 4.23 (q, J=7.0 Hz, 2H), 2.28 (q, J=7.5 Hz, 2H), 1.29 (t, J=7.0 Hz, 3H), 0.95 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 569.1 (M+H+).

Sources & evidence

ORD record
ord-4a75260199a844b4bb2d32857dd93f22
Source dataset
uspto-grants-2014_12
Patent number
US08921565B2

Reaction notes

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