Phenol → 6-(4-Chlorophenyl)-1-methyl-7-phenoxy-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepine

HRID 2401403Notes

Reaction equation

HRID 2401403 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:22]([O:23][CH3:24])=[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.[C:25]1(O)[CH:30]=[CH:29]C=[CH:27][CH:26]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:22]([O:23][C:24]4[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=4)=[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

Participants

3

Reactant 2

HCID 996PhenolHCID 573445186-(4-chlorophenyl)-7-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepine2×

Product 1

HCID 573889316-(4-Chlorophenyl)-1-methyl-7-phenoxy-4H-isoxazolo[5,4-c]pyrido[4,3-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 phenol was used instead of methanol. LC/MS m/z 402 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.33 (d, J=5.40 Hz, 1H), 7.56 (d, J=5.40 Hz, 1H), 7.41 (s, 4H), 7.31 (tt, J=2.20, 8.00 Hz, 2H), 7.14 (tt, J=1.40, 7.50 Hz, 1H), 6.79 (d, J=8.00 Hz, 2H), 5.31 (d, J=13.3 Hz, 1H), 4.25 (d, J=13.29 Hz, 1H), 2.58 (s, 3H).

Sources & evidence

ORD record
ord-6200cdcae8734179a0a02360d3cbdfd2
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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