6-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[4,5-e]pyrido[3,4-c]azepine → 6-(4-Chlorophenyl)-8-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepine

HRID 2401411Notes

Reaction equation

HRID 2401411 reaction equation
ClC1C=CC(C2C3C(OC)=NC=CC=3C3C(C)=N[O:15][C:12]=3CN=2)=CC=1.Cl[C:26]1[CH:27]=[CH:28][C:29]2[C:30]3[C:46]([CH3:47])=[N:45][O:44][C:31]=3[CH2:32][N:33]=[C:34]([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)[C:35]=2[N:36]=1.ClC1C=CC(C2C3C(F)=NC=CC=3C3C(C)=NOC=3CN=2)=CC=1>>[Cl:43][C:40]1[CH:41]=[CH:42][C:37]([C:34]2[C:35]3[N:36]=[C:26]([O:15][CH3:12])[CH:27]=[CH:28][C:29]=3[C:30]3[C:46]([CH3:47])=[N:45][O:44][C:31]=3[CH2:32][N:33]=2)=[CH:38][CH:39]=1

Participants

4

Reactant 3

HCID 573445176-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[4,5-e]pyrido[3,4-c]azepineHCID 573445186-(4-chlorophenyl)-7-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepine2×HCID 866667278-Chloro-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepine2×

Product 1

HCID 679513066-(4-Chlorophenyl)-8-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepine

Procedure

A procedure similar to 6-(4-Chlorophenyl)-7-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepine (Compound 170) was followed, except that 8-chloro-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepine (Compound 240) was used as starting material instead of 6-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[4,5-e]pyrido[3,4-c]azepine. LC/MS m/z 340 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.31 (d, J=8.31 Hz, 1H), 7.83 (d, J=8.31 Hz, 1H), 7.43 (td, J=2.30, 8.70 Hz, 2H), 7.35 (td, J=2.30, 8.70 Hz, 2H), 4.79 (br. s, 2H), 3.34 (s, 3H), 2.53 (s, 3H).

Sources & evidence

ORD record
ord-3d823ccb69fe4150beed2b7045a7b1d9
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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