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

HRID 552216ノート

反応式

HRID 552216 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  1. customThe reaction was quenched
  2. additiontreated

出典と根拠

ORDレコード
ord-2db14ead8e3c4741a3b6a4412b386772
出典データセット
uspto-grants-2011_05
特許番号
US07951801B2

反応ノート

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