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

HRID 2401412Notes

Reaction equation

HRID 2401412 reaction equation
ClC1C=CC([C:8]2C3C(NC)=NC=CC=3C3C(C)=NOC=3C[N:14]=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]([NH:14][CH3:8])[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 573445216-(4-chlorophenyl)-N,1-dimethyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-7-amine2×HCID 866667278-Chloro-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepine2×

Product 1

HCID 679513006-(4-Chlorophenyl)-N,1-dimethyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepin-8-amine

Procedure

A procedure similar to 6-(4-chlorophenyl)-N,1-dimethyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-7-amine (Compound 173) 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 339 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 7.83 (d, J=8.72 Hz, 1H), 7.41 (td, J=2.10, 8.50 Hz, 2H), 7.36 (td, J=2.10, 8.50 Hz, 2H), 6.96 (q, J=4.50 Hz, 1H), 6.77 (d, J=8.93 Hz, 1H), 4.61 (br. s, 2H), 2.62 (d, J=4.78 Hz, 3H), 2.46 (s, 3H).

Sources & evidence

ORD record
ord-9165e5556adf4c24a5568a939b8daac5
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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