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2-Bromoisonicotinic acid → 2-Bromo-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-isonicotinamide

HRID 51847
Notes
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Reaction equation

HRID 51847 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]([N:47]([CH2:49][CH2:50][O:51][CH3:52])[CH3:48])=[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]([N:47]([CH2:49][CH2:50][O:51][CH3:52])[CH3:48])=[CH:39][CH:38]=[C:37]([O:36][CH3:35])[C:42]=2[N:43]=1)=[O:7]
ParticipantsProcedureSources & evidenceReaction notes

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 220157444-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine

Product 1

HCID 227369762-Bromo-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-isonicotinamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent
HCID 8028TetrahydrofuranSolvent
HCID 312751,4-DioxaneSolvent

Procedure

From 2-bromo-isonicotinic acid, HATU and N-diethylisopropylamine in THF, then treatment with 4-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine in dioxane and DMF. ES-MS m/e (%): 453 (M{81Br}+H+, 100), 451 (M{79Br}+H+, 71).

Sources & evidence

ORD record
ord-4b3600d8800145a48b03ee2044472bac
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713499B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes