HCID 66859549, compound → HCID 46864591, compound

HRID 1803234Notes

Reaction equation

HRID 1803234 reaction equation
[CH2:1]([N:4]1[C:8]([CH:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH2:10]C=C)=[N:7][C:6]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[C:31]([Cl:33])[N:30]=[CH:29]3)=[C:24]([O:34][CH3:35])[CH:23]=2)=[N:5]1)[CH:2]=[CH2:3]>CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[Cl:33][C:31]1[N:30]=[CH:29][N:28]([C:25]2[CH:26]=[CH:27][C:22]([NH:21][C:6]3[N:7]=[C:8]4[CH:9]([C:13]5[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=5[Cl:20])[CH2:10][CH:3]=[CH:2][CH2:1][N:4]4[N:5]=3)=[CH:23][C:24]=2[O:34][CH3:35])[CH:32]=1

Participants

3

Reactant 1

HCID 66859549HCID 66859549, compound

Product 1

HCID 46864591HCID 46864591, compoundYield 136.7%

Reagents, catalysts & solvents 1

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalyst

Procedure

1-Allyl-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-5-(1-(2,4-dichlorophenyl)but-3-enyl)-1H-1,2,4-triazol-3-amine (450 mg, 0.094 mmol) was subjected to a ring closing metathesis procedure analogous to Step C of Example 1 (160° C., 15 min, 25 mol % Hoveyda-Grubbs Catalyst 2nd Generation) to afford (Z)—N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-9-(2,4-dichlorophenyl)-8,9-dihydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine (64.5 mg, 15% yield) as a dark brown solid. LC-MS (M+H)+=501.1. 1H NMR (500 MHz, chloroform-d) δ ppm 7.51 (d, J=1.53 Hz, 1 H) 7.45 (d, J=2.14 Hz, 1 H) 7.39 (d, J=2.14 Hz, 1 H) 7.25-7.30 (m, 1 H) 7.21-7.25 (m, 1 H) 7.09 (d, J=−8.55 Hz, 1 H) 7.02 (d, J=1.53 Hz, 1 H) 6.80 (dd, J=8.39, 2.29 Hz, 1 H) 6.63 (s, 1 H) 5.99-6.10 (m, 2 H) 4.81-5.01 (m, 3 H) 3.79 (s, 3 H) 2.78-2.97 (m, 1 H) 2.58-2.78 (m, 1 H).

Sources & evidence

ORD record
ord-8bfa84a3070a48f596c0cc459d453bef
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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