HCID 15169762, compound → 1-(Naphthalen-1-yl)butane-1,3-dionato

HRID 2165468Notes

Reaction equation

HRID 2165468 reaction equation
N1(CC2N(N)[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3OC2)CCOCC1.N1(CC2CN(N)C3C=[CH:34][CH:35]=[CH:36][C:28]=3[O:27]2)CCCCC1.C(N(CC1CN(N)[C:46]2[CH:50]=CC=[CH:53][C:45]=2O1)CC)C.NCC1CN(N)C2C=CC=CC=2[O:57]1.CNCC1CN(N)C2C=CC=CC=2O1.N1(CC2CN(N)C3C=CC=CC=3O2)CCSCC1.N1(CC2CN(N)C3C=CC=CC=3O2)CCCC1.N1(CC2CN(N)C3C=CC=CC=3O2)CCC1.CN1CCN(CC2CN(N)C3C=CC=CC=3O2)CC1.N1CCCNCC1CC1CN(N)C2C=CC=CC=2O1.COC1C=CC(C(=O)CC(=O)CC)=CC=1>>[C:15]1([C:28](=[O:27])[CH2:36][C:35](=[O:57])[CH3:34])[C:12]2[C:11](=[CH:53][CH:45]=[CH:46][CH:50]=2)[CH:18]=[CH:17][CH:16]=1

Participants

12

Reactant 11

HCID 15169762HCID 15169762, compoundHCID 15169783HCID 15169783, compoundHCID 53661485HCID 53661485, compoundHCID 53678843HCID 53678843, compoundHCID 53850509HCID 53850509, compoundHCID 54074517HCID 54074517, compoundHCID 54115875HCID 54115875, compoundHCID 54259664HCID 54259664, compoundHCID 54431175HCID 54431175, compoundHCID 54453717HCID 54453717, compoundHCID 67909372HCID 67909372, compound

Product 1

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

Procedure

Proceeding in a manner similar to that described in Example 2A above, substituting for the 3-(4-morpholinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine used therein a molar equivalent amount of 2-(1-piperidinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine, 2-(N,N-diethylaminomethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine, 2-aminomethyl-4-amino-3,4-dihydro-2H-1,4-benzoxazine, 2-methylaminomethyl-4-amino-3,4-dihydro-2H-1,4-benzoxazine, 2-(4-thiomorpholinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine, 2-(1-pyrrolidinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine, 2-(1-azetidinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine, 2-(4-methyl-1-piperazinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine or 2-[1-(hexahydro-4H-1,4-diazepinyl)methyl]-4-amino-3,4-dihydro-2H-1,4-benzoxazine, and substituting for the 5-(4-methoxyphenyl)-3,5-pentanedione used therein a molar equivalent amount of 4-(1-naphthyl)-2,4-butanedione, there can be obtained, respectively, 2-(1-piperidinylmethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, 2-(N,N-diethylaminomethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, 2-(aminomethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, 2-(methylaminomethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, 2-(4-thiomorpholinylmethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, 2-(1-pyrrolidinylmethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, 2-(1-azetidinylmethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine, 2-(4-methyl-1-piperazinylmethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine or 2-[1-(hexahydro-4H-1,4-diazepinyl)methyl]-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine.

Sources & evidence

ORD record
ord-e8f58d4ecf724f548cfb66d46805c4c6
Source dataset
uspto-grants-1990_07
Patent number
US04939138

Reaction notes

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