Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=O)=[CH:5][CH:4]=1.CN(C=O)C.C(N=C=NCCCN(C)C)C.[NH2:35][C:36]1[S:37][C:38]2[CH:44]=[C:43]([N+:45]([O-:47])=[O:46])[CH:42]=[CH:41][C:39]=2[N:40]=1>>[N+:45]([C:43]1[CH:42]=[CH:41][C:39]2[N:40]=[C:36]([NH:35][C:12](=[O:14])[C:11]3[CH:15]=[CH:16][CH:17]=[N:18][C:10]=3[NH:9][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[S:37][C:38]=2[CH:44]=1)([O-:47])=[O:46]Participants
5
Conditions
- Temperature
- 27 °C
Procedure
To a stirred solution of 2-(4-methoxy phenylamino)nicotinic acid (29, 244 mg 1 mmol) in dry DMF (10 mL) hydroxy benzotriazole HOBt (1.2 mmol) were added at 0° C. After 10 min 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) (1.2 mmol) was added and finally 2-amino-6-nitrobenzothiazole (37, 137 mg, 0.7 mmol) were added, then the resulting mixture was stirred at room temperature (27° C.) for 8-10 h and then the reaction mixture was quenched with NaHCO3 and extracted in ethyl acetate (4×25 mL) from the ice cold aqueous layer and dried over anhydrous Na2SO4. The resulting product (5) was purified by column chromatography employing EtOAc/Hexane as an eluent.
Workup
- customthe reaction mixture was quenched with NaHCO3
- extractionextracted in ethyl acetate (4×25 mL) from the ice cold aqueous layer
- dry with materialdried over anhydrous Na2SO4
- customThe resulting product (5) was purified by column chromatography
Sources & evidence
- ORD record
- ord-82b42c78ccde425e9db9537b997fb2f6
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029553B2
Linked notes
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