Toluene → N,N-diisopropyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamide

HRID 724214

Reaction equation

C1(C)C=CC=CC=1.C([Li])CCC.Br[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]([N:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[O:25])[CH:18]=[CH:17]2.CON(C)C(C[C:39]1[N:40]=[CH:41][N:42]([C:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:43]=1)=O.C1C[O:67][CH2:66]C1>O>[CH:27]([N:26]([CH:30]([CH3:32])[CH3:31])[C:24]([C:19]1[CH:18]=[CH:17][C:16]2[C:21](=[CH:22][CH:23]=[C:14]([C:66]([C:39]3[N:40]=[CH:41][N:42]([C:44]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[CH:43]=3)=[O:67])[CH:15]=2)[CH:20]=1)=[O:25])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: -70 °C

Procedure

Dry toluene (20 ml) was cooled to −70° C. and n-butyl lithium (1.6 M; 2.35 ml) was added dropwise. A solution of 6-bromo-N,N-diisopropyl-2-naphthamide (1.20 g) in dry THF (8 ml) was added dropwise to the reaction mixture. After stirring the mixture at −70° C. for 20 min, a solution of N-methoxy-N-methyl-1-trityl-1H-imidazole-4-carboxyamide (1.09 g) in dry THF (6 ml) was added dropwise to the reaction mixture. The mixture was stirred at −70° C. for 20 min and water was added at the same temperature to stop the reaction. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (hexane:ethyl acetate=2:1) to give the title compound (1.40 g) as a colorless powder. The physical and chemical data were identical with those obtained for the compound obtained of Reference Example 13.

Workup

stirringThe mixture was stirred at −70° C. for 20 min
customthe reaction
extractionThe mixture was extracted with ethyl acetate
washthe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-f83ff25fe42847548c13016112ee2d90
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141598B2

Linked notes

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