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

HRID 12216Notes

Reaction equation

HRID 12216 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.

Workup

  1. customThe reaction was quenched
  2. additiontreated

Sources & evidence

ORD record
ord-0ba7be200a0745fa8dcb6c2a37b8dd3a
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Reaction notes

Loading…