4-Fluorobenzoic Acid → 4-Fluoro-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-benzamide

HRID 1611941Notes

Reaction equation

HRID 1611941 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:46][C:44]2[O:45][C:41]3[C:40]([CH:47]4[CH2:48][CH2:49][O:50][CH2:51][CH2:52]4)=[CH:39][CH:38]=[C:37]([O:36][CH3:35])[C:42]=3[N:43]=2)=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 99734-Fluorobenzoic 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 222522604-Fluoro-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-benzamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

From 4-fluorobenzoic 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 (%): 371 (M+H+, 100).

Sources & evidence

ORD record
ord-1f8d658c6f394d6eb4dbe56d3b40b4e1
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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