2-Methylpyridine-4-carboxylic acid → N-[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-2-methyl-isonicotinamide

HRID 1611943Notes

Reaction equation

HRID 1611943 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.[CH3:35][O:36][C:37]1[C:42]2[N:43]=[C:44]([NH2:46])[O:45][C:41]=2[C:40]([CH:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)=[CH:39][CH:38]=1>C1COCC1.O1CCOCC1.CN(C=O)C>[CH3:35][O:36][C:37]1[C:42]2[N:43]=[C:44]([NH:46][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][N:10]=[C:2]([CH3:1])[CH:3]=3)[O:45][C:41]=2[C:40]([CH:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)=[CH:39][CH:38]=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 222522334-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine

Product 1

HCID 10338955N-[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-2-methyl-isonicotinamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

From 2-methylisonicotinic acid, HATU and N-diethylisopropylamine in THF, then treatment with 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl-amine in dioxane and DMF. ES-MS m/e (%): 368 (M+H+, 100).

Sources & evidence

ORD record
ord-e522f48354b74086ad41006403f91637
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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