6-(4-chlorophenyl)-7-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepine → 6-(4-Chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepin-8(9H)-one

HRID 2401419Notes

Reaction equation

HRID 2401419 reaction equation
ClC1C=CC(C2C3C=CC(=O)NC=3C3C(C)=NOC=3CN=2)=CC=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:32]3[CH:45]=[C:44]([O:46]C)[N:43]=[CH:42][C:33]=3[C:34]3[C:40]([CH3:41])=[N:39][O:38][C:35]=3[CH2:36][N:37]=2)=[CH:27][CH:26]=1.ClC1N=CC2C3C(C)=NOC=3CN=C(C3C=CC(Cl)=CC=3)C=2C=1.ClC1C=CC(C2C3C(OC)=NC=CC=3C3C(C)=NOC=3CN=2)=CC=1.ClC1C=CC(C2C3C=CC(OC)=NC=3C3C(C)=NOC=3CN=2)=CC=1>>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:32]3[C:33](=[CH:42][NH:43][C:44](=[O:46])[CH:45]=3)[C:34]3[C:40]([CH3:41])=[N:39][O:38][C:35]=3[CH2:36][N:37]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 5

HCID 573445186-(4-chlorophenyl)-7-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepineHCID 678131525-(4-chlorophenyl)-2-methoxy-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepineHCID 678187195-(4-Chlorophenyl)-10-methyl-1H-isoxazolo[5,4-c]pyrido[2,3-e]azepin-2(7H)-oneHCID 679712506-(4-chlorophenyl)-8-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepineHCID 866667288-Chloro-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepine

Product 1

HCID 679513056-(4-Chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepin-8(9H)-one

Procedure

A procedure similar to 5-(4-chlorophenyl)-10-methyl-1H-isoxazolo[5,4-c]pyrido[2,3-e]azepin-2(7H)-one was followed, except that 6-(4-chlorophenyl)-8-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepine (prepared from 8-chloro-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepine in a similar fashion to 6-(4-chlorophenyl)-7-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepine) was used as starting material instead of 5-(4-chlorophenyl)-2-methoxy-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepine. LC/MS m/z 326 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 12.45 (br. s, 1H), 7.92 (br. s, 1H), 7.48 (s, 4H), 6.25 (br. s, 1H), 4.78 (br. s, 2H), 2.43 (s, 3H).

Sources & evidence

ORD record
ord-af216a2c2cb94d29944d7cd87c6f94b2
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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