Ethyl Acetate → N-(6-chloro-4-methyl-9H-beta-carbolin-8-yl)-nicotinamide

HRID 12223

反応式

HRID 12223 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:15])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([CH3:16])[C:5]2=1.Cl.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1.CCOC(C)=O>N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=3)[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([CH3:16])[C:5]2=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 593375486-chloro-4-methyl-9H-beta-carbolin-8-ylamine

生成物 1

HCID 11302139N-(6-chloro-4-methyl-9H-beta-carbolin-8-yl)-nicotinamide収率 8.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 1049Pyridine溶媒

実験手順

A solution of 6-chloro-4-methyl-9H-β-carbolin-8-ylamine (43 mg, 0.19 mmol) in pyridine (4 ml) was stirred at RT under an argon atmosphere. Nicotinoyl chloride hydrochloride (40 mg, 0.22 mmol) was added thereto and the reaction mixture was stirred for 12 hr. The solution was diluted with H2O (5 ml) and poured into a separatory funnel containing H2O (5 ml) and EtOAc (25 ml). The reaction mixture was shaken and the layers were separated. The aqueous layer was extracted with EtOAc (2×25 ml). The combined organic layers were washed with a saturated sodium bicarbonate solution (15 ml), followed by brine, then dried over MgSO4, filtered, and concentrated to yield N-(6-chloro-4-methyl-9H-β-carbolin-8-yl)-nicotinamide (5.2 mg) as an orange viscous oil.

後処理

  1. additionpoured into a separatory funnel
  2. stirringThe reaction mixture was shaken
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc (2×25 ml)
  5. washThe combined organic layers were washed with a saturated sodium bicarbonate solution (15 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-6ae8c9d0d8654400b65d536d16c21f9b
出典データセット
uspto-grants-2010_06
特許番号
US07727985B2

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