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N,N'-Dimethylethylenediamine → N-(4-tert-Butylbenzyl)-6-cyano-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 1961479
ノート
印刷プレビュー

反応式

HRID 1961479 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=1)=[O:14])=[CH:5]2.[CH3:27][NH:28]CCNC.[C-]#N.[Na+]>C1(C)C=CC=CC=1.[NH4+].[OH-].[Cu]I>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:13]([C:6]2[C:7]([CH3:12])=[N:8][C:9]3[C:4]([CH:5]=2)=[CH:3][C:2]([C:27]#[N:28])=[CH:11][N:10]=3)=[O:14])=[CH:18][CH:19]=1)([CH3:26])([CH3:25])[CH3:24]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8070N,N'-DimethylethylenediamineHCID 8929Sodium CyanideHCID 667460516-bromo-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide

生成物 1

HCID 66745491N-(4-tert-Butylbenzyl)-6-cyano-2-methyl-1,8-naphthyridine-3-carboxamide収率 32%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 1140Toluene溶媒
HCID 14923Ammonium Hydroxide溶媒

反応条件

温度
120 °C

実験手順

6-Bromo-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide (90 mg, 0.22 mmol), N,N′-dimethylethane-1,2-diamine (24 μl, 0.22 mmol), CuI (4 mg, 0.02 mmol), KI (7 mg, 0.04 mmol) and NaCN (13 mg, 0.26 mmol) were suspended in toluene (2 ml). The mixture was stirred at 120° C. for 48 hours in a closed high-pressure flask. The reaction was cooled, diluted with NH4OH (30 ml) and extracted with CH2Cl2 (3*30 ml). Combined organics were washed with water (30 ml), dried over MgSO4 and evaporated. The product was purified by flash chromatography using CH2Cl2/CH3OH (25:1) as eluent to give 25 mg (32%) of the title compound as pale solids.

後処理

  1. temperatureThe reaction was cooled
  2. extractionextracted with CH2Cl2 (3*30 ml)
  3. washCombined organics were washed with water (30 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe product was purified by flash chromatography

出典と根拠

ORDレコード
ord-8b5e0e3d624d4393b68dc326982bc5d0
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415333B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート