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

HRID 2102312Notes

Reaction equation

HRID 2102312 reaction equation
ClC1C=C(C2ON=C(CN3CCCCN4C(C5C=CN=CC=5)=NN=C34)N=2)C=CC=1.Cl[CH2:31][C:32]1[N:36]=[C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=2)[O:34][N:33]=1.[F:44][C:45]([F:57])([F:56])[C:46]1[N:50]2[CH2:51][CH2:52][CH2:53][CH2:54][NH:55][C:49]2=[N:48][N:47]=1>CC(=O)OCC>[Cl:43][C:39]1[CH:38]=[C:37]([C:35]2[O:34][N:33]=[C:32]([CH2:31][N:55]3[CH2:54][CH2:53][CH2:52][CH2:51][N:50]4[C:46]([C:45]([F:57])([F:44])[F:56])=[N:47][N:48]=[C:49]34)[N:36]=2)[CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 100825203-(Chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazoleHCID 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 1354658283-(Trifluoromethyl)-5H,6H,7H,8H,9H-[1,2,4]triazolo[4,3-a][1,3]diazepine

Product 1

HCID 112117039-{[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-3-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepineYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 3-(chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole (89 mg, 0.39 mmol), 3-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-α][1,3]diazepine (73 mg, 0.35 mmol. Column chromatography (hep./EA 1:1) afforded 85 mg (61%) of the title compound. 1H NMR: 1.88 (m, 2H), 1.94 (m, 2H), 3.26-3.35 (m, 2H), 3.98-4.07 (m, 2H), 4.83 (s, 2H), 7.46 (m, 1H), 7.50-7.57 (m, 1H), 7.98 (m, 1H), 8.09 (m, 1H)

Sources & evidence

ORD record
ord-0f9943f668ce4f43b190a5dcfca099b6
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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