2-Bromoisonicotinic acid → 2-Bromo-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamide

HRID 1582108Notes

Reaction equation

HRID 1582108 reaction equation
[Br: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])[S: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>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([NH:46][C:44]1[S:45][C:41]2[C:40]([CH:47]3[CH2:48][CH2:49][O:50][CH2:51][CH2:52]3)=[CH:39][CH:38]=[C:37]([O:36][CH3:35])[C:42]=2[N:43]=1)=[O:7]

Participants

7

Reactant 3

HCID 2227012-Bromoisonicotinic acidHCID 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 227195382-Bromo-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

From 2-bromo-isonicotinic acid, HATU and N-diethylisopropylamine in THF, then treatment with 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-ylamine in dioxane and DMF. ES-MS m/e (%): 450 (M{81Br}+H+, 100), 448 (M{79Br}+H+, 85).

Sources & evidence

ORD record
ord-9723a3889931403fbdd77119595a1a7e
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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