Ammonia → 6-chloro-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide
Reaction equation
[Cl:1][C:2]1[C:10]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:9]2[C:5]([CH:6]=[C:7]([C:21](O)=[O:22])[NH:8]2)=[CH:4][CH:3]=1.[N:24]1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Cl:1][C:2]1[C:10]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:13])=[O:14])=[C:9]2[C:5]([CH:6]=[C:7]([C:21]([NH2:24])=[O:22])[NH:8]2)=[CH:4][CH:3]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a mixture of 6-chloro-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.69 g), 1H-1,2,3-benzotriazol-1-ol (0.31 g) and N,N-dimethylformamide (10 ml) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.44 g) at room temperature, and the mixture was stirred at 50° C. for 20 min, and allowed to cool to room temperature. 28% Aqueous ammonia (0.30 ml) was added, and the reaction mixture was stirred at room temperature for 2 hr, and acidified with 10% aqueous citric acid solution. The resulting crystals were filtrated, washed with water, and dried to give the title compound (0.70 g, quantitative) as colorless crystals. melting point 225-226° C. (decomposition).
Workup
- temperatureto cool to room temperature
- stirringthe reaction mixture was stirred at room temperature for 2 hr
- filtrationThe resulting crystals were filtrated
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-0d1d72f439eb492eb7a004dcd34fa447
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652133B2
Reaction notes
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