6-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[4,5-e]pyrido[3,4-c]azepine → 5-(4-Chlorophenyl)-N,10-dimethyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepin-2-amine

HRID 2401406Notes

Reaction equation

HRID 2401406 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:22](NC)=[N:21][CH:20]=[CH:19][C:10]=3[C:11]3[C:17]([CH3:18])=[N:16][O:15][C:12]=3[CH2:13][N:14]=2)=[CH:4][CH:3]=1.ClC1C=CC2C(C3C=CC(Cl)=CC=3)=[N:34][CH2:33]C3ON=C(C)C=3C=2N=1.ClC1C=CC(C2C3C(F)=NC=CC=3C3C(C)=NOC=3CN=2)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:10]=[CH:19][C:20]([NH:34][CH3:33])=[N:21][C:22]=3[C:11]3[C:17]([CH3:18])=[N:16][O:15][C:12]=3[CH2:13][N:14]=2)=[CH:4][CH:3]=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-amineHCID 573889332-Chloro-5-(4-chlorophenyl)-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepine

Product 1

HCID 573889325-(4-Chlorophenyl)-N,10-dimethyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepin-2-amine

Procedure

A procedure similar to 6-(4-chlorophenyl)-N,1-dimethyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-7-amine was followed, except that 2-chloro-5-(4-chlorophenyl)-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepine 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 7.42 (td, J=2.30, 8.70 Hz, 2H), 7.39-7.35 (m, 3H), 7.22 (d, J=8.72 Hz, 1H), 6.41 (d, J=8.93 Hz, 1H), 4.63 (br. s, 2H), 2.91 (d, J=4.57 Hz, 3H), 2.58 (s, 3H).

Sources & evidence

ORD record
ord-5648d645931c4b74893a3c125b510b5f
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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