4-Fluorobenzoic Acid → 4-Fluoro-N-{4-methoxy-7-[(4-methoxy-benzyl)-methyl-amino]-benzothiazol-2-yl}-benzamide

HRID 51884Notes

Reaction equation

HRID 51884 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+].[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1.[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](O)=[O:37])=[CH:34][CH:33]=1.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>[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH:12][C:10]2[S:11][C:7]3[C:6]([N:13]([CH2:27][C:26]4[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=4)[CH3:14])=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)=[O:37])=[CH:34][CH:33]=1

Participants

9

Reactant 6

HCID 99734-Fluorobenzoic AcidHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 81531DiisopropylethylamineHCID 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 101737634-Fluoro-N-{4-methoxy-7-[(4-methoxy-benzyl)-methyl-amino]-benzothiazol-2-yl}-benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

From 4-methoxy-N7-methyl-benzothiazole-2,7-diamine with potassium carbonate and 4-methoxybenzyl chloride in DMF, then treatment with 4-fluorobenzoic acid, HATU and N-ethyldiisopropylamine in THF. ES-MS m/e (0/o): 452 (M+H+, 100).

Sources & evidence

ORD record
ord-df8228a60b184128aa35fd93c2b66c95
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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