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

HRID 2401415Notes

Reaction equation

HRID 2401415 reaction equation
Cl[C:2]1C=CC(C2C3C(=O)N(C)C=CC=3C3C(C)=NOC=3CN=2)=CC=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[C:33]3[NH:46][C:45](=[O:47])[CH:44]=[CH:43][C:34]=3[C:35]3[C:41]([CH3:42])=[N:40][O:39][C:36]=3[CH2:37][N:38]=2)=[CH:28][CH:27]=1.ClC1C=CC(C2C3C(=O)NC=CC=3C3C(C)=NOC=3CN=2)=CC=1>>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[C:33]3[N:46]([CH3:2])[C:45](=[O:47])[CH:44]=[CH:43][C:34]=3[C:35]3[C:41]([CH3:42])=[N:40][O:39][C:36]=3[CH2:37][N:38]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 573896756-(4-chlorophenyl)-1,8-dimethyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-7(8H)-oneHCID 679512466-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepin-8(7H)-oneHCID 1359818826-(4-chlorophenyl)-1-methyl-4H-isoxazolo[4,5-e]pyrido[3,4-c]azepin-7(8H)-one

Product 1

HCID 679513046-(4-Chlorophenyl)-1,7-dimethyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepin-8(7H)-one

Procedure

A procedure similar to 6-(4-chlorophenyl)-1,8-dimethyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-7(8H)-one was followed, except that 6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,2-e]azepin-8(7H)-one was used as starting material instead of 6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-7(8H)-one. LC/MS m/z 340 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 7.98 (d, J=9.56 Hz, 1H), 7.48 (d, J=8.93 Hz, 2H), 7.35 (d, J=8.52 Hz, 2H), 6.82 (d, J=9.35 Hz, 1H), 5.32 (d, J=12.46 Hz, 1H), 4.15 (d, J=12.7 Hz, 1H), 2.95 (s, 3H), 2.50 (s, 3H).

Sources & evidence

ORD record
ord-af2017aa0bb04f19be5e27ee9e823f03
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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