2-methylpyridine-4-carboxylic Acid Hydrochloride → N-[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-2-methyl-isonicotinamide

HRID 1582109Notes

Reaction equation

HRID 1582109 reaction equation
Cl.[CH3:2][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])[S: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>[CH3:36][O:37][C:38]1[C:43]2[N:44]=[C:45]([NH:47][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][N:11]=[C:3]([CH3:2])[CH:4]=3)[S: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

Participants

7

Reactant 3

HCID 27628242-methylpyridine-4-carboxylic Acid HydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 220157354-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl-amine

Product 1

HCID 22719556N-[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-2-methyl-isonicotinamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

From 2-methyl-isonicotinic acid hydrochloride, HATU and N-diethylisopropylamine in THF, then treatment with 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl-amine in dioxane and DMF. ES-MS m/e (%): 406 (M+Na+, 46), 384 (M+H+, 100).

Sources & evidence

ORD record
ord-9359993c4f514f6e9a1ea2dc530caded
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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