1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-beta-carbolin-8-yl]-2-methyl-nicotinamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([Cl:22])[CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[CH:11]=[N:10][CH:9]=[C:8]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[C:7]2=1.[CH3:23][C:24]1[N:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](O)=[O:27].CCN=C=NCCCN(C)C>N1C=CC=CC=1>[Cl:22][C:4]1[CH:5]=[C:6]2[C:14](=[C:2]([NH:1][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][CH:31]=[N:32][C:24]=3[CH3:23])[CH:3]=1)[NH:13][C:12]1[CH:11]=[N:10][CH:9]=[C:8]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[C:7]2=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
N-(8-amino-6-chloro-9H-β-carbolin-4-yl)-2,2,2-trifluoro-acetamide (90 mg, 0.274 mmol, 1 equiv.) and 2-methylnicotinic acid (45 mg, 0.329 mmol, 1.2 equiv.) were dissolved in 1.5 ml of anhydrous pyridine under N2. EDCI (84 mg, 0.438 mmol, 1.6 equiv.) was added in one portion and the reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched with water and the resulting dark solids captured by filtration. These solids were titurated in a 3:1 methanol—DMSO solution to give N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-β-carbolin-8-yl]-2-methyl-nicotinamide as light yellow solids (41 mg, 3%). 1H-NMR (300 MHz, DMSO-d6): δ 11.94 (br, 1H), 11.78 (s, 1H), 10.61 (s, 1), 9.00 (s, 1), 8.64 (d, 1), 8.38 (s, 1H), 8.13 (d, 1), 8.01 (s, 1H), 7.73 (s, 1H), 7.45 (m, 1H), 2.68 (s, 3H). Formic acid standard conditions. DAD RT=1.98 min. M+H=448.
Workup
- customThe reaction was quenched with water
- filtrationthe resulting dark solids captured by filtration
Sources & evidence
- ORD record
- ord-8e8bd2d63eea4d92ab5d94d67caec3ba
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951801B2
Reaction notes
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