Methylhydrazine → HCID 178428083, compound

HRID 873930Notes

Reaction equation

HRID 873930 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]([O:15]CC)=O)[C:11](=O)[C:10](=[O:19])[N:9]2[C:20]2[CH:25]=[C:24]([CH3:26])[C:23](=[O:27])[N:22]([CH3:28])[CH:21]=2)=[CH:4][CH:3]=1.[CH3:29][NH:30][NH2:31]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:12]3[C:11](=[N:31][N:30]([CH3:29])[C:13]=3[OH:15])[C:10](=[O:19])[N:9]2[C:20]2[CH:25]=[C:24]([CH3:26])[C:23](=[O:27])[N:22]([CH3:28])[CH:21]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 117702882HCID 117702882, compound

Product 1

HCID 178428083HCID 178428083, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in analogy to the procedure described for Example 57 using ethyl 2-(4-chlorophenyl)-1-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-4,5-dioxopyrrolidine-3-carboxylate (Step 73.2) and methyl hydrazine at reflux for 32 hr. tR: 0.68 min (LC-MS 2); ESI-MS: 385 [M+H]+, ESI-MS: 383 [M−H]− (LC-MS 2); Rf=0.23 (CH2Cl2/7.5% MeOH/1% AcOH); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.90 (s, 3H) 3.34 (s, 3H) 3.44 (m, 3H) 5.62 (s, 1H) 7.09 (d, J=8.6 Hz, 2H) 7.17-7.34 (m, 3H) 7.60 (d, J=2.7 Hz, 1H).

Workup

  1. temperatureat reflux for 32 hr

Sources & evidence

ORD record
ord-6ec14b8aba1548afb3e72f191b10545a
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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