4-Fluorobenzoic Acid → N-[7-(acetyl-methyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=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.[NH2:44][C:45]1[S:46][C:47]2[C:53]([N:54]([CH3:58])[C:55](=[O:57])[CH3:56])=[CH:52][CH:51]=[C:50]([O:59][CH3:60])[C:48]=2[N:49]=1>C1COCC1>[C:55]([N:54]([CH3:58])[C:53]1[C:47]2[S:46][C:45]([NH:44][C:6](=[O:8])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)=[N:49][C:48]=2[C:50]([O:59][CH3:60])=[CH:51][CH:52]=1)(=[O:57])[CH3:56]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 31 mg (0.22 mmol) 4-fluoro-benzoic acid in 2 ml THF were added 89 mg (0.23 mmol) HATU and 0.07 ml (0.44 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 2 h. 28 mg (0.11 mmol) N-(2-amino-4-methoxy-benzothiazol-7-yl)-N-methyl-acetamide was then added and stirring continued at 50° C. for 16 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (dichloromethane/methanol 50/1) followed by trituration in ether afforded 10 mg (24%) N-[7-(acetyl-methyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide as a white crystalline solid. ES-MS m/e (%o): 374 (M+H+, 100).
Workup
- stirringstirring
- waitcontinued at 50° C. for 16 h
- concentrationThe reaction mixture was then concentrated in vacuo
Sources & evidence
- ORD record
- ord-0b0f7ecae25c451f9a7ec9cddc2bb9d0
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713499B2
Reaction notes
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