4-Chlorobenzaldehyde → 4-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one

HRID 873948Notes

Reaction equation

HRID 873948 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:32])[CH3:31])[C:24](OCC)=[O:25]>>[C:30]([C:29]1[CH:18]([C:17]2[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=2)[N:12]([C:8]2[CH:9]=[C:10]([CH3:11])[C:5]3[N:6]([C:2]([CH3:1])=[N:3][N:4]=3)[CH:7]=2)[C:24](=[O:25])[C:23]=1[OH:22])(=[O:32])[CH3:31]

Participants

4

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 69208Ethyl 2,4-dioxovalerateHCID 753574493,8-Dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-amine

Product 1

HCID 1177026714-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one

Procedure

The title compound was prepared in analogy to the procedure described in Step 84.5 using 3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-amine (Step 67.4), 4-chlorobenzaldehyde and ethyl 2,4-dioxovalerate. tR: 0.70 min (LC-MS 2); ESI-MS: 397 [M+H]+ (LC-MS 2); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3H) 2.44 (s, 3H) 2.63 (s, 3H) 6.14 (s, 1H) 7.27 (d, J=8.4 Hz, 2H) 7.33-7.40 (m, 3H) 8.53 (s, 1H).

Sources & evidence

ORD record
ord-39aa9883ab5a490abcd9bfb3ba257c4f
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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