Ethyl 2,4-dioxovalerate → 4-Acetyl-1-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-5-(3-(trifluoromethoxy)-phenyl)pyrrolidine-2,3-dione

HRID 873950Notes

Reaction equation

HRID 873950 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[F:11][C:12]([F:23])([F:22])[O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O.CC[O:26][C:27]([C:29]([CH2:31][C:32]([CH3:34])=[O:33])=[O:30])=O>>[C:32]([CH:31]1[CH:17]([C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([O:13][C:12]([F:23])([F:22])[F:11])[CH:15]=2)[N:1]([C:2]2[CH:3]=[C:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)[C:27](=[O:26])[C:29]1=[O:30])(=[O:33])[CH3:34]

Participants

4

Reactant 3

HCID 69208Ethyl 2,4-dioxovalerateHCID 6051393-(Trifluoromethoxy)benzaldehydeHCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-one

Product 1

HCID 1177028004-Acetyl-1-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-5-(3-(trifluoromethoxy)-phenyl)pyrrolidine-2,3-dione

Procedure

The title compound was prepared in analogy to the procedure described in Step 57.1 using 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 20.2), 3-trifluoromethoxy-benzaldehyde and ethyl acetopyruvate at 110° C. for 4 hr. tR: 0.79 min (LC-MS 2); ESI-MS: 423 [M+H]+ (LC-MS 2); ESI-MS: 421 [M−H]− (LC-MS 2).

Sources & evidence

ORD record
ord-405877128b844bf3a8479f0b310a1cde
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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