Pyrrolidine → 6-(4-Chlorophenyl)-1-methyl-8-(pyrrolidin-1-yl)-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepine

HRID 2401418Notes

Reaction equation

HRID 2401418 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:22]=[C:21]([NH:23][CH3:24])[N: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.N1C[CH2:28][CH2:27][CH2:26]1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:22]=[C:21]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:24]4)[N: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 31268PyrrolidineHCID 678178606-(4-Chlorophenyl)-N,1-dimethyl-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepin-8-amine

Product 1

HCID 678171866-(4-Chlorophenyl)-1-methyl-8-(pyrrolidin-1-yl)-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepine

Procedure

A procedure similar to 6-(4-chlorophenyl)-N,1-dimethyl-4H-isoxazolo[5,4-c]pyrido[3,4-e]azepin-8-amine was followed, except that pyrrolidine was used instead of methylamine (33% in EtOH). LC/MS m/z 379 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.56 (d, J=0.62 Hz, 1H), 7.48 (ddd, J=1.70, 2.50, 8.20 Hz, 2H), 7.44 (ddd, J=1.70, 2.50, 8.20 Hz, 2H), 6.23 (d, J=0.62 Hz, 1H), 4.66 (br. s, 2H), 3.36-3.32 (m, 4H), 2.49 (s, 3H), 1.98-1.83 (m, 4H).

Sources & evidence

ORD record
ord-1548a575007d42d384f6a3dfcb89c8bc
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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