2-Methylpyridine-4-carboxylic acid → N-[7-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-2-methyl-isonicotinamide

HRID 1611952Notes

Reaction equation

HRID 1611952 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[C:50]3[O:49][C:48]([NH2:51])=[N:47][C:46]=3[C:45]([O:52][CH3:53])=[CH:44][CH:43]=2)=[CH:38][CH:37]=1>C1COCC1.O1CCOCC1.CN(C=O)C>[F:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[C:50]3[O:49][C:48]([NH:51][C:5](=[O:7])[C:4]4[CH:8]=[CH:9][N:10]=[C:2]([CH3:1])[CH:3]=4)=[N:47][C:46]=3[C:45]([O:52][CH3:53])=[CH:44][CH:43]=2)=[CH:40][CH:41]=1

Participants

7

Reactant 3

HCID 27628212-Methylpyridine-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222522347-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-ylamine

Product 1

HCID 10022458N-[7-(4-Fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-2-methyl-isonicotinamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

From 2-methyl-isonicotinic acid, HATU and N-diethylisopropylamine in THF, then treatment with 7-(4-fluoro-phenyl)-4-methoxy-benzooxazol-2-yl-amine in dioxane and DMF. ES-MS m/e (%): 378 (M+H+, 100).

Sources & evidence

ORD record
ord-68f99d2d95cb4e0d98ee44af17d4cebc
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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