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

HRID 1961479
Notes
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Reaction equation

HRID 1961479 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 1140TolueneSolvent
HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8b5e0e3d624d4393b68dc326982bc5d0
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415333B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes