Chloride → 7,8-bis(4-chlorophenyl)-2-ethyl-5-morpholino-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

HRID 271433Notes

Reaction equation

HRID 271433 reaction equation
ClC1N2[C:8](=[O:11])NN=C2C(C2C=CC(Cl)=CC=2)=C(C2C=CC(Cl)=CC=2)N=1.[Cl-].ICC.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:42]=[C:41]([N:43]3[CH2:46][C:45](NCC)(C(N)=O)[CH2:44]3)[N:40]3[C:53](=[O:58])[N:54]([CH2:56][CH3:57])[N:55]=[C:39]3[C:38]=2[C:59]2[CH:64]=[CH:63][C:62]([Cl:65])=[CH:61][CH:60]=2)=[CH:33][CH:32]=1>>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:42]=[C:41]([N:43]3[CH2:46][CH2:8][O:11][CH2:45][CH2:44]3)[N:40]3[C:53](=[O:58])[N:54]([CH2:56][CH3:57])[N:55]=[C:39]3[C:38]=2[C:59]2[CH:60]=[CH:61][C:62]([Cl:65])=[CH:63][CH:64]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 4

HCID 312ChlorideHCID 6340IodoethaneHCID 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 159531487,8-bis(4-chlorophenyl)-2-ethyl-5-morpholino-[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 iodoethane, 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=4.306 min, [M+H]30 =470.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-61937105215b408ea0c1af20155e5936
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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