Chloride → 5-(azetidin-1-yl)-7,8-bis(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

HRID 271438Notes

Reaction equation

HRID 271438 reaction equation
ClC1N2C(=O)NN=C2C(C2C=CC(Cl)=CC=2)=C(C2C=CC(Cl)=CC=2)N=1.[Cl-].Cl[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]([F:38])([F:37])[F:36])=[N:33][CH:34]=1.[Cl:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[N:51]=[C:50]([N:52]3[CH2:55][C:54](NCC)(C(N)=O)[CH2:53]3)[N:49]3[C:62](=[O:67])[N:63](CC)[N:64]=[C:48]3[C:47]=2[C:68]2[CH:73]=[CH:72][C:71]([Cl:74])=[CH:70][CH:69]=2)=[CH:42][CH:41]=1>>[N:52]1([C:50]2[N:49]3[C:62](=[O:67])[N:63]([CH2:28][C:29]4[CH:34]=[N:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=4)[N:64]=[C:48]3[C:47]([C:68]3[CH:69]=[CH:70][C:71]([Cl:74])=[CH:72][CH:73]=3)=[C:46]([C:43]3[CH:44]=[CH:45][C:40]([Cl:39])=[CH:41][CH:42]=3)[N:51]=2)[CH2:53][CH2:54][CH2:55]1

Participants

5

Reactant 4

HCID 312ChlorideHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 159530981-(7,8-Bis(4-chlorophenyl)-2-ethyl-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)-3-(ethylamino)azetidine-3-carboxamideHCID 587728405-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Product 1

HCID 159532445-(azetidin-1-yl)-7,8-bis(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Procedure

The title compound was prepared in two steps from 5-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one by nucleophilic displacement of chloride with the requisite amine, followed by alkylation with 5-(chloromethyl)-2-(trifluoromethyl)pyridine, in a manner analogous to that in which 1-(7,8-bis(4-chlorophenyl)-2-ethyl-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)-3-(ethylamino)azetidine-3-carboxamide was prepared. HPLC/MS: retention time=4.483 min, [M+H]30 =571.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-10c2946f61dd4726975f3fb31e632225
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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