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

HRID 873982Notes

Reaction equation

HRID 873982 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.[CH:22]1([C:25](=[O:34])[CH2:26][C:27](=[O:33])[C:28](OCC)=[O:29])[CH2:24][CH2:23]1>>[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:28](=[O:29])[C:27]([OH:33])=[C:26]2[C:25]([CH:22]2[CH2:24][CH2:23]2)=[O:34])=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 16779961Ethyl 4-cyclopropyl-2,4-dioxobutanoateHCID 753574493,8-Dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-amine

Product 1

HCID 1177026275-(4-chlorophenyl)-4-(cyclopropanecarbonyl)-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 4-cyclopropyl-2,4-dioxobutanoate. tR: 0.82 min (LC-MS 2); ESI-MS: 483 [M+H]+ (LC-MS 2); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.60-0.97 (m, 4H) 2.41 (s, 3H) 2.55-2.68 (m, 3H) 2.85-2.93 (m, 1H) 6.12 (s, 1H) 7.11-7.28 (m, 2H) 7.28-7.41 (m, 3H) 8.50 (s, 1H) —OH missing.

Sources & evidence

ORD record
ord-0d54cc18b43b414e821c1073f8afb011
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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