Methyl 1-bromomethyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthoate → 7-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one

HRID 1061886Notes

Reaction equation

HRID 1061886 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:41])([C:17]3[N:18]=[CH:19][N:20]([C:22]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:21]=3)[CH:14]([CH3:16])[CH3:15])=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:42]([O:44]C)=O.CO.[CH3:48][NH2:49]>C1COCC1>[OH:41][C:13]([C:9]1[CH:10]=[CH:11][C:12]2[C:3]3[CH2:2][N:49]([CH3:48])[C:42](=[O:44])[C:4]=3[CH:5]=[CH:6][C:7]=2[CH:8]=1)([C:17]1[N:18]=[CH:19][N:20]([C:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:21]=1)[CH:14]([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 22285061Methyl 1-bromomethyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthoateHCID 57454252Monomethylamine methanol

Product 1

HCID 101670197-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-bromomethyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthoate (0.80 g) was dissolved in THF (8 ml) and 40% methylamine methanol solution (8 ml) was added. The reaction mixture was stirred at room temperature for 20 hrs. and the solvent was evaporated. The residue was suspended in ethyl acetate and filtrated to give 7-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one as a colorless solid (0.77 g). This solid was suspended in a mixed solution of THF and methanol (1:3, 20 ml) and pyridine hydrochloride (0.23 g) was added. The reaction mixture was stirred with heating at 60° C. for 6 hrs., and the solvent was evaporated. The residue was diluted with saturated aqueous sodium hydrogen carbonate and extracted twice with ethyl acetate-THF (1:1). The organic layers were combined, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from THF-methanol to give the title compound as colorless crystals (0.28 g).

Workup

  1. customand the solvent was evaporated
  2. filtrationfiltrated

Sources & evidence

ORD record
ord-5379927cbc6c44258e94519f3b305ffa
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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