Methyl iodide → HCID 70874045, compound

HRID 1526123Notes

Reaction equation

HRID 1526123 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.N1CCCC[CH2:18]1.[NH2:23][C:24](=[S:51])[C:25]([C:49]#[N:50])=[CH:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]2)=[CH:29][C:28]=1[N+:46]([O-:48])=[O:47].CI>C(O)(=O)C.C(O)C>[C:49]([C:25]1[CH:26]([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])[CH2:35][CH2:34]3)=[CH:29][C:28]=2[N+:46]([O-:48])=[O:47])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[NH:23][C:24]=1[S:51][CH3:18])#[N:50]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8082PiperidineHCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl esterHCID 86709584HCID 86709584, compound

Product 1

HCID 70874045HCID 70874045, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

0.55 g (2.5 mmol) of ethyl 3-(4-methoxyphenyl)-3-oxopropanoate, 10 ml of ethanol and 0.3 ml (3 mmol) of piperidine are added respectively to 1 g (2.5 mmol) of tert-butyl 4-(4-(3-amino-2-cyano-3-thioxoprop-1-enyl)-3-nitrophenyl)piperazine-1-carboxylate. The reaction mixture is stirred at room temperature for 5 h and then 0.31 ml (5 mmol) of methyl iodide is added. After 12 h of stirring, 3 ml of acetic acid is added and the reaction medium is carried at 50° C. for 24 hours. After returning to room temperature, the solvents are evaporated and the residue is purified by silica gel chromatography (eluent: 3:7 cyclohexane/ethyl acetate) to yield 1.3 g (83%) of tert-butyl 4-(4-(3-cyano-5-(ethoxycarbonyl)-6-(4-methoxyphenyl)-2-(methylthio)-1,4-dihydropyridine-4-yl)-3-nitrophenyl)piperazine-1-carboxylate in the form of a light yellow powder.

Workup

  1. stirringAfter 12 h of stirring
  2. waitthe reaction medium is carried at 50° C. for 24 hours
  3. customAfter returning to room temperature
  4. customthe solvents are evaporated
  5. customthe residue is purified by silica gel chromatography (eluent: 3:7 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-ee9c64bd50824729a49239508ade2cf3
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

Loading…