1-Acetylnaphthalene → Win 551212 mesylate

HRID 1196189Notes

Reaction equation

HRID 1196189 reaction equation
[N:1]1([CH2:7][CH:8]2[N:13](N)[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[O:10][CH2:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:19]1([C:29](=[O:34])[CH2:30][C:31](=O)[CH3:32])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.[N+](C1C=[C:40]([S:44]([OH:47])(=[O:46])=[O:45])C=CC=1)([O-])=O.N1C=CC=CC=1.C1(C(C)=O)C2C(=CC=CC=2)C=CC=1.[H-].[Na+]>CN(C=O)C.C1(C)C=CC=CC=1.C(OCC)C.C(O)C.C(OCC)(=O)C>[CH3:40][S:44]([OH:47])(=[O:46])=[O:45].[N:1]1([CH2:7][CH:8]2[N:13]3[C:31]([CH3:32])=[C:30]([C:29]([C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=[CH:21][CH:20]=4)=[O:34])[C:15]4[CH:16]=[CH:17][CH:18]=[C:11]([C:12]=43)[O:10][CH2:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

11

Reactant 5

HCID 136631-AcetylnaphthaleneHCID 24758Sodium hydrideHCID 12118017HCID 12118017, compoundHCID 15169762HCID 15169762, compoundHCID 193668001-(Naphthalen-1-yl)butane-1,3-dionato

Product 1

HCID 19366775Win 551212 mesylate

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following a procedure similar to that described in Example 2A above, (+)-3-(4-morpholinylmethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine methanesulfonate (11.6 g from methanol/diethyl ether), m.p. 256° C.-259° C., [α]D25 =+40.2° (1% in DMF) was prepared by reaction of 15.5 g (0.062 mole) of (+)-3-(4-morpholinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine with 15.8 g (0.075 mole) of 4-(1-naphthyl)-2,4-butanedione in 500 ml of toluene in the presence of a catalytic amount of pyridine 3-nitrobenzenesulfonate (the 2,4-diketone being prepared by reaction of methyl 1-naphthyl ketone with ethyl acetate in the presence of sodium hydride and ethanol in diethyl ether), followed by cyclization of the resulting hydrazone by refluxing the latter in 300 ml of glacial acetic acid and recrystallization of the product from methanol/ diethyl ether.

Workup

  1. temperatureby refluxing the
  2. customlatter in 300 ml of glacial acetic acid and recrystallization of the product from methanol/ diethyl ether

Sources & evidence

ORD record
ord-87cf86ab27924a63b78b713ec836e5a9
Source dataset
uspto-grants-1992_05
Patent number
US05112820

Reaction notes

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