2-((4S)-6-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-4-yl)acetamide → 2-((4S)-7-Amino-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-4-yl)acetamide

HRID 2401420Notes

Reaction equation

HRID 2401420 reaction equation
ClC1C=CC(C2C3C=CC(N)=NC=3C3C(C)=NOC=3C[N:14]=2)=CC=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:32]3[C:49](F)=[N:48][CH:47]=[CH:46][C:33]=3[C:34]3[C:44]([CH3:45])=[N:43][O:42][C:35]=3[C@H:36]([CH2:38][C:39]([NH2:41])=[O:40])[N:37]=2)=[CH:27][CH:26]=1.ClC1C=CC2C(C3C=CC(Cl)=CC=3)=NCC3ON=C(C)C=3C=2N=1>CS(C)=O.CCO>[NH2:14][C:49]1[C:32]2[C:31]([C:28]3[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=3)=[N:37][C@@H:36]([CH2:38][C:39]([NH2:41])=[O:40])[C:35]3[O:42][N:43]=[C:44]([CH3:45])[C:34]=3[C:33]=2[CH:46]=[CH:47][N:48]=1

Participants

6

Reactant 3

HCID 573445262-((4S)-6-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-4-yl)acetamideHCID 573889332-Chloro-5-(4-chlorophenyl)-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepineHCID 678147955-(4-Chlorophenyl)-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepin-2-amine

Product 1

HCID 679513832-((4S)-7-Amino-6-(4-chlorophenyl)-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-4-yl)acetamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

A procedure similar to 5-(4-chlorophenyl)-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepin-2-amine was followed, except that a solution of 2-((4S)-6-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-4-yl)acetamide in DMSO was used instead of a solution of 2-chloro-5-(4-chlorophenyl)-10-methyl-7H-isoxazolo[5,4-c]pyrido[2,3-e]azepine in EtOH. LC/MS m/z 382 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.21 (d, J=5.19 Hz, 1H), 7.67 (br. s, 1H), 7.38 (td, J=2.30, 8.70 Hz, 2H), 7.33 (td, J=2.30, 8.70 Hz, 2H), 7.04 (br. s, 1H), 6.95 (d, J=5.19 Hz, 1H), 5.89 (br. s, 2H), 4.40 (dd, J=6.54, 8.00 Hz, 1H), 3.27 (dd, J=8.00 Hz, 15.60, 1H), 3.11 (dd, J=6.65, 15.58 Hz, 1H), 2.49 (s, 3H).

Sources & evidence

ORD record
ord-36b74130e090414a9224a7efbd4cbb18
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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