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

HRID 1196192Notes

Reaction equation

HRID 1196192 reaction equation
N1(CC2N(N)[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3OC2)CCOCC1.C(N(CC1CN(N)C2C=[CH:33][CH:34]=[CH:35][C:27]=2[O:26]1)CC)C.NCC1CN(N)[C:41]2[CH:45]=CC=[CH:48][C:40]=2O1.CNCC1CN(N)C2C=CC=CC=2[O:53]1.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:27](=[O:26])[CH2:35][C:34](=[O:53])[CH3:33])[C:12]2[C:11](=[CH:48][CH:40]=[CH:41][CH:45]=2)[CH:18]=[CH:17][CH:16]=1

Participants

11

Reactant 10

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 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-5 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-thiomorpholinyl-methyl)-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-c569bc320fce4be399580d987ae07d40
Source dataset
uspto-grants-1992_05
Patent number
US05112820

Reaction notes

Loading…