6-(1,2-epoxyethyl)-2-phenyl-4H-1,3-dioxino[5,4-b]pyridine → N-[[4-[4-[[6-[[2-Hydroxy-2-(2-phenyl-4H-1,3-dioxino[5,4-b]pyridin-6-yl]ethyl](phenylmethyl)amino]hexyl]oxy]-1-butynyl]phenyl]methyl]pentanamide

HRID 1165273

Reaction equation

HRID 1165273 reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]1[N:9]=[C:8]2[CH2:10][O:11][CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][C:7]2=[CH:6][CH:5]=1.[C:20]1([CH2:26][NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][C:37]#[C:38][C:39]2[CH:44]=[CH:43][C:42]([CH2:45][NH:46][C:47](=[O:52])[CH2:48][CH2:49][CH2:50][CH3:51])=[CH:41][CH:40]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[OH:1][CH:2]([C:4]1[N:9]=[C:8]2[CH2:10][O:11][CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][C:7]2=[CH:6][CH:5]=1)[CH2:3][N:27]([CH2:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][C:37]#[C:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:45][NH:46][C:47](=[O:52])[CH2:48][CH2:49][CH2:50][CH3:51])=[CH:43][CH:44]=1

Participants

4

Reactant 2

HCID 137484036-(1,2-epoxyethyl)-2-phenyl-4H-1,3-dioxino[5,4-b]pyridineHCID 19862690N-[[4-[4-[[6-[(phenylmethyl)amino]hexyl]oxy]-1-butynyl]phenyl]methyl]pentanamide

Product 1

HCID 19862666N-[[4-[4-[[6-[[2-Hydroxy-2-(2-phenyl-4H-1,3-dioxino[5,4-b]pyridin-6-yl]ethyl](phenylmethyl)amino]hexyl]oxy]-1-butynyl]phenyl]methyl]pentanamideYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-oxiranyl-2-phenyl-4H-1,3-dioxino[5,4-b]pyridine (0.712 g) and N-[[4-[4-[[6-[(phenylmethyl)amino]hexyl]oxy]-1-butynyl]phenyl]methyl]pentanamide (1.25 g) in methanol (10 ml) was refluxed for 1l h. The methanol was evaporated to leave an oil which was purified by FCC eluting with ER to give the title compound as a yellow oil (1.02 g), t.l.c. ER:triethylamine (100:1) Rf 0.2

Workup

  1. customThe methanol was evaporated
  2. customto leave an oil which
  3. customwas purified by FCC
  4. washeluting with ER

Sources & evidence

ORD record
ord-db31c16490614ef982ad91ad7706ae8e
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Linked notes

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