HCID 12118017, compound → Win 551212 mesylate

HRID 1031272Notes

Reaction equation

HRID 1031272 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>CN(C=O)C.C1(C)C=CC=CC=1.C(O)(=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

7

Reactant 3

HCID 12118017HCID 12118017, compoundHCID 15169762HCID 15169762, compoundHCID 193668001-(Naphthalen-1-yl)butane-1,3-dionato

Product 1

HCID 19366775Win 551212 mesylate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

Similarly (-)-3-(4-morpholinylmethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine methanesulfonate (7.2 g), m.p. 256°-260° C., [α]D25 =-39.4° (1% in DMF) was prepared by reaction of 9.3 g (0.037 mole) of (-)3-(4-morpholinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine with 9.5 g (0.045 mole) of 4-(1-naphthyl)-2,4-butanedione in toluene in the presence of a catalytic amount of pyridine 3-nitrobenzenesulfonate followed by cyclization of the resulting hydrazone by refluxing in glacial acetic acid and recrystallization of the product from methanol/diethyl ether.

Workup

  1. customrecrystallization of the product from methanol/diethyl ether

Sources & evidence

ORD record
ord-acd586bbb381436aa9707d41c574b570
Source dataset
uspto-grants-1992_04
Patent number
US05109135

Reaction notes

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