9-{[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine → 9-{1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl}-3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine

HRID 2102310Notes

Reaction equation

HRID 2102310 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH2:13][N:14]3[CH2:20][CH2:19][CH2:18][CH2:17][N:16]4[C:21]([C:24]5[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=5)=[N:22][N:23]=[C:15]34)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:30]S(OC(C1N=C(C2C=CC=C(Cl)C=2)ON=1)C)(=O)=O.N1C=CC(C2N3CCCCNC3=NN=2)=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]([N:14]3[CH2:20][CH2:19][CH2:18][CH2:17][N:16]4[C:21]([C:24]5[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=5)=[N:22][N:23]=[C:15]34)[CH3:30])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 113503199-{[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepineHCID 578379891-[5-(3-Chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethyl methanesulfonateHCID 1361224673-(Pyridin-4-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine

Product 1

HCID 112587149-{1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl}-3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepineYield 4%

Procedure

The title compound was prepared analogous to 9-{[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine from 1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl methanesulfonate (186 mg, 0.61 mmol), 3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine (200 mg, 0.56 mmol) to give 8.1 mg (4%) of the title compound. 1H NMR: 1.83 (d, 3H), 1.86-1.95 (m, 4H), 3.16-3.27 (m, 1H), 3.43-3.53 (m, 1H), 3.75-3.87 (m, 1H), 3.95-4.07 (m, 1H), 5.54 (q, 1H), 7.41-7.52 (m, 3H), 7.52-7.58 (m, 1H), 8.01 (m, 1H), 8.12 (m, 1H), 8.73 (m, 2H).

Sources & evidence

ORD record
ord-705df98757e14643b8ae034afcb8d62e
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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