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

HRID 1961479
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HRID 1961479 반응식
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]
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참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 1140Toluene용매
HCID 14923Ammonium Hydroxide용매

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8b5e0e3d624d4393b68dc326982bc5d0
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415333B2

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