4-Chlorobenzaldehyde → 5-(4-Chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-propionylpyrrolidine-2,3-dione

HRID 873923Notes

Reaction equation

HRID 873923 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[C:8]([NH2:12])[CH:9]=[C:10]([CH3:11])[C:5]2=[N:4][N:3]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.[O:22]=[C:23]([CH2:29][C:30](=[O:33])[CH2:31][CH3:32])[C:24](OCC)=[O:25]>>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]2[N:12]([C:8]3[CH:9]=[C:10]([CH3:11])[C:5]4[N:6]([C:2]([CH3:1])=[N:3][N:4]=4)[CH:7]=3)[C:24](=[O:25])[C:23](=[O:22])[CH:29]2[C:30](=[O:33])[CH2:31][CH3:32])=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 61590Ethyl-2,4-dioxohexanoateHCID 753574493,8-Dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-amine

Product 1

HCID 1177025355-(4-Chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-propionylpyrrolidine-2,3-dione

Procedure

The title compound was prepared in analogy to the procedure described in Step 60.1 using 3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-amine (Step 67.4), 4-chlorobenzaldehyde and ethyl 2,4-dioxohexanoate at 110° C. for 4 hr. tR: 0.79 min (LC-MS 2); ESI-MS: 411 [M+H]+, ESI-MS: 409 [M−H]− (LC-MS 2).

Sources & evidence

ORD record
ord-fe943cfbb64b427e989c837b385014f6
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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