Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 2-Chloromethyl-N-[7-(4-fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-isonicotinamide

HRID 1611951Notes

Reaction equation

HRID 1611951 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][N:11]=1)[C:6]([OH:8])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[C:51]3[O:50][C:49]([NH2:52])=[N:48][C:47]=3[C:46]([O:53][CH3:54])=[CH:45][CH:44]=2)=[CH:39][CH:38]=1>C1COCC1.O1CCOCC1.CN(C=O)C>[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][N:11]=1)[C:6]([NH:52][C:49]1[O:50][C:51]2[C:43]([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)=[CH:44][CH:45]=[C:46]([O:53][CH3:54])[C:47]=2[N:48]=1)=[O:8]

Participants

7

Reactant 3

HCID 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-ylamineHCID 222522422-(Chloromethyl)isonicotinic acid

Product 1

HCID 100930682-Chloromethyl-N-[7-(4-fluoro-phenyl)-4-methoxy-benzooxazol-2-yl]-isonicotinamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

From 2-chloromethyl-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 (%): 414 (M{37Cl}+H+, 30), 412 (M{35Cl}+H+, 100).

Sources & evidence

ORD record
ord-19c0b62d110848ed80e2f0d0aced5ea6
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

Loading…