HCID 86591272, compound → HCID 22341409, compound

HRID 585002Notes

Reaction equation

HRID 585002 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[C:17]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:18]=[C:19]([CH2:21][N:22]([CH3:32])[C:23](=[O:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:20]=3)=[CH:11][CH:10]=2)[S:3]1.[H][H]>O1CCOCC1>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[C:17]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:18]=[C:19]([CH2:21][N:22]([CH3:32])[C:23](=[O:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:20]=3)=[CH:11][CH:10]=2)[S:3]1

Participants

4

Reactant 2

HCID 86591272HCID 86591272, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22341409HCID 22341409, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a manner similar to that of Example 1(g), starting with 370 mg (7 mmol) of N-[4″-(2,4-dioxothiazolidin-5-ylidene-methyl)[1,1′;3′,1″]terphenyl-5′-ylmethyl]-N-methyl-octanamide in 5 ml of dioxane and under 3 atm of hydrogen, and after purification by chromatography on a column of silica eluted with a heptane/ethyl acetate mixture (6/4), 170 mg (47%) of N-[4″-(2,4-dioxo-thiazolidin-5-ylmethyl)[1,1′;3′,1″]terphenyl-5′-yl-methyl]-N-methyloctanamide are obtained in the form of a pale yellow foam.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a heptane/ethyl acetate mixture (6/4), 170 mg (47%) of N-[4″-(2,4-dioxo-thiazolidin-5-ylmethyl)[1,1′;3′,1″]terphenyl-5′-yl-methyl]-N-methyloctanamide
  3. customare obtained in the form of a pale yellow foam

Sources & evidence

ORD record
ord-a48d6bab268948d4bf7a1837ea65bd98
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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