HCID 15389740, compound → HCID 178440877, compound

HRID 2373749Notes

Reaction equation

HRID 2373749 reaction equation
[ClH:1].CC(C1C=C(C=C(C(C)(C)C)C=1O)C(NC1C=CC([NH:18][C:19]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=N)=CC=1)=O)(C)C.CC(C1C=C([C:49](=[CH2:61])[C:50]([NH:52][C:53]2[CH:58]=[CH:57][C:56]([OH:59])=[C:55]([NH2:60])[CH:54]=2)=[O:51])C=C(C(C)(C)C)C=1O)(C)C.[CH3:62][C:63]([C:66]1[CH:67]=[C:68]([CH:79]=[C:80]([C:83]([CH3:86])([CH3:85])[CH3:84])[C:81]=1[OH:82])C(NC1C=CC(N)=CC=1)=O)([CH3:65])[CH3:64]>>[ClH:1].[CH3:86][C:83]([C:80]1[CH:79]=[C:68]([CH:61]=[CH:49][C:50]([NH:52][C:53]2[CH:58]=[CH:57][C:56]([OH:59])=[C:55]([NH:60][C:19]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[NH:18])[CH:54]=2)=[O:51])[CH:67]=[C:66]([C:63]([CH3:64])([CH3:65])[CH3:62])[C:81]=1[OH:82])([CH3:85])[CH3:84]

Participants

4

Reactant 3

HCID 15389740HCID 15389740, compoundHCID 86584206HCID 86584206, compoundHCID 178441077HCID 178441077, compound

Product 1

HCID 178440877HCID 178440877, compoundYield 62%

Procedure

The experimental protocol used is the same as that described for compound 1, with 3-[(3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-N-(4-hydroxy-3-aminophenyl)-2-propenamide replacing the 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-(4-aminophenyl)-benzamide. The free base is purified on a silica column (eluant: heptane/ethyl acetate: 35/65). The pure fractions are collected and concentrated under reduced pressure. The evaporation residue is diluted in 10 ml of acetone and salified with a molar solution of HCl in anhydrous ether, as described previously. 0.35 g (62%) of a yellow powder is obtained. Melting point: 199-200° C.

Workup

  1. customThe free base is purified on a silica column (eluant: heptane/ethyl acetate: 35/65)
  2. customThe pure fractions are collected
  3. concentrationconcentrated under reduced pressure
  4. additionThe evaporation residue is diluted in 10 ml of acetone

Sources & evidence

ORD record
ord-3b52734a15a6483fb5b90c4734128a7d
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

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