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

HRID 1961479Notes

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]

Participants

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

temperatureThe reaction was cooled
extractionextracted with CH2Cl2 (3*30 ml)
washCombined organics were washed with water (30 ml)
dry with materialdried over MgSO4
customevaporated
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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