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

HRID 1611944Notes

Reaction equation

HRID 1611944 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.[CH3:36][O:37][C:38]1[C:43]2[N:44]=[C:45]([NH2:47])[O:46][C:42]=2[C:41]([CH:48]2[CH2:53][CH2:52][O:51][CH2:50][CH2:49]2)=[CH:40][CH:39]=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:47][C:45]1[O:46][C:42]2[C:41]([CH:48]3[CH2:49][CH2:50][O:51][CH2:52][CH2:53]3)=[CH:40][CH:39]=[C:38]([O:37][CH3:36])[C:43]=2[N:44]=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 222522334-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamineHCID 222522422-(Chloromethyl)isonicotinic acid

Product 1

HCID 222522352-chloromethyl-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-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 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl-amine in dioxane and DMF. ES-MS m/e (%): 404 (M{37Cl}+H+, 30), 402 (M{35Cl}+H+, 100).

Sources & evidence

ORD record
ord-467f624b5cfb4855ab59c4c9d2e4b273
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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