Benzyl Bromide → N-[7-(Benzyl-methyl-amino)-4-methoxy-benzothiazol-2-yl]-2-methyl-isonicotinamide

HRID 51872

Reaction equation

HRID 51872 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([NH:13][CH3:14])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.[CH3:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][N:39]=1)[C:34](O)=[O:35].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C.C1COCC1>[CH2:21]([N:13]([CH3:14])[C:6]1[C:7]2[S:11][C:10]([NH:12][C:34](=[O:35])[C:33]3[CH:37]=[CH:38][N:39]=[C:31]([CH3:30])[CH:32]=3)=[N:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

9

Reactant 6

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 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 227369784-methoxy-N7-methyl-benzothiazole-2,7-diamine

Product 1

HCID 10151026N-[7-(Benzyl-methyl-amino)-4-methoxy-benzothiazol-2-yl]-2-methyl-isonicotinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

From 4-methoxy-N7-methyl-benzothiazole-2,7-diamine with potassium carbonate and benzyl bromide in DMF, then treatment with 2-methyl-isonicotinic acid hydrochloride, HATU and N-ethyldiisopropylamine in THF. ES-MS m/e (%): 419 (M+H+, 100).

Sources & evidence

ORD record
ord-ee19fed81d054f7e9638c543dd0a1caa
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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