1,1'-Carbonyldiimidazole → 5-Acetylthiophene-2-carboxylic acid (2-amino-3-carbamoylphenyl)amide
Reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:26][C:27]1[C:35]([NH2:36])=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([NH2:31])=[O:30]>N1C=CC=CC=1.CN(C)C=O>[NH2:26][C:27]1[C:28]([C:29](=[O:30])[NH2:31])=[CH:32][CH:33]=[CH:34][C:35]=1[NH:36][C:9]([C:7]1[S:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1)=[O:11]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 45 °C
Procedure
To a solution of 5-acetylthiophene-2-carboxylic acid (1.80 g, 10.55 mmol) in pyridine (12 mL) and N,N-dimethylformamide (12 mL) was added 1,1′-carbonyldiimidazole (1.88 g, 11.60 mmol) and the mixture stirred at 45° C. for 4 hours. 2,3-Diaminobenzamide dihydrochloride (synthesized as described in U.S. Pat. No. 6,737,421, column 11, EXAMPLE 2, step (e), 2.36 g, 10.55 mmol) was added and the mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The resulting yellow solid was collected by filtration, washed with water and ethyl acetate and dried to give the title compound (2.91 g, 91%). MS (APCI): 304 (M+1)+.
Workup
- addition6,737,421, column 11, EXAMPLE 2, step (e), 2.36 g, 10.55 mmol) was added
- stirringthe mixture was stirred at ambient temperature overnight
- concentrationThe reaction mixture was concentrated
- customthe residue partitioned between ethyl acetate and water
- filtrationThe resulting yellow solid was collected by filtration
- washwashed with water and ethyl acetate
- customdried
Sources & evidence
- ORD record
- ord-ac3744e0456f4fa2b15e8b887e355057
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595406B2
Reaction notes
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