Water → N-(6-chloro-7-methylsulfanyl-9H-beta-carbolin-8-yl)-2-methyl-nicotinamide

HRID 12200

反応式

HRID 12200 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:17])[C:14]=1[S:15][CH3:16])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[CH3:18][C:19]1[N:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22].Cl.CN(C)CCCN=C=NCC.O>N1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:17][C:21](=[O:22])[C:20]3[CH:24]=[CH:25][CH:26]=[N:27][C:19]=3[CH3:18])[C:14]=1[S:15][CH3:16])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

参加物

7

反応物 4

HCID 962WaterHCID 6433732-Methylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 671666356-chloro-7-methylsulfanyl-9H-beta-carbolin-8-ylamine2 回

生成物 1

HCID 11361077N-(6-chloro-7-methylsulfanyl-9H-beta-carbolin-8-yl)-2-methyl-nicotinamide収率 89.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

A 250 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-methylsulfanyl-9H-β-carbolin-8-ylamine (Intermediate 28, 2.336 g, 8.86 mmol) and 2-methylnicotinic acid (3.219 g, 23.4 mmol) in 80 ml anhydrous pyridine. To the resulting reaction mixture at RT was added solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (7.080 g, 36.9 mmol) and the reaction mixture was heated to 100° C. (oil bath) for 2 days. The resulting mixture was cooled to RT and concentrated (rotavap) to afford a brown residue. The residue was redissolved in MeOH (50 ml), slowly added to a stirring mixture of 5:1 H2O/saturated aqueous sodium bicarbonate (600 mlL) and stirred at RT for ˜18 hr. The precipitated solid was collected via suction filtration, washed with Et2O (2×150 ml), and air-dried to afford 3.036 g of crude N-(6-chloro-7-methylsulfanyl-9H-β-carbolin-8-yl)-2-methyl-nicotinamide as a brown solid. The crude material was purified via HPLC (yields=˜40-60%)

後処理

  1. customTo the resulting reaction mixture at RT
  2. temperatureThe resulting mixture was cooled to RT
  3. concentrationconcentrated (rotavap)
  4. customto afford a brown residue
  5. filtrationThe precipitated solid was collected via suction filtration
  6. washwashed with Et2O (2×150 ml)
  7. customair-dried

出典と根拠

ORDレコード
ord-fe7796a45668470a88b977caac4dbba7
出典データセット
uspto-grants-2010_06
特許番号
US07727985B2

関連ノート

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