1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-beta-carbolin-8-yl]-nicotinamide

HRID 552216Notes

Reaction equation

HRID 552216 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.C[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][CH:24]=3)[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=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6433732-Methylnicotinic acidHCID 86595095N-(8-amino-6-chloro-9H-beta-carbolin-4-yl)-2,2,2-trifluoro-acetamide

Product 1

HCID 86595097N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-beta-carbolin-8-yl]-nicotinamideYield 32%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 (40 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 2 hours. The reaction was quenched and treated following the preceding protocol to obtain 38 mg (32%) of N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-β-carbolin-8-yl]-nicotinamide. 1H-NMR (300 MHz, DMSO-d6): δ 11.89 (br, 1H), 10.73 (s, 1), 9.28 (s, 1), 8.97 (s, 1), 8.84 (d, 1), 8.43 (d, 1), 8.37 (s, 1), 7.85 (s, 1), 7.76 (s, 1), 7.67 (m, 1). Formic acid standard conditions. DAD RT=1.94 min. M+H=434.

Workup

  1. customThe reaction was quenched
  2. additiontreated

Sources & evidence

ORD record
ord-2db14ead8e3c4741a3b6a4412b386772
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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