Hydrochloric Acid → 2-[6-Amino-4-[4-(ethylamino)-3-hydroxyphenyl]-5-(hydroxymethyl)-2-pyridinyl]-3-(cycloproylmethoxy)phenol

HRID 2218267Notes

Reaction equation

HRID 2218267 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([NH:17][CH2:18][CH3:19])=[C:14]([OH:16])[CH:15]=2)[CH:5]=[C:4]([C:20]2[C:25]([O:26]CC3C=CC(OC)=CC=3)=[CH:24][CH:23]=[CH:22][C:21]=2[O:36][CH2:37][CH:38]2[CH2:40][CH2:39]2)[N:3]=1.Cl>O1CCOCC1.C(OCC)C>[NH2:1][C:2]1[N:3]=[C:4]([C:20]2[C:21]([O:36][CH2:37][CH:38]3[CH2:40][CH2:39]3)=[CH:22][CH:23]=[CH:24][C:25]=2[OH:26])[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([NH:17][CH2:18][CH3:19])=[C:14]([OH:16])[CH:15]=2)[C:7]=1[CH2:8][OH:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 691449515-[2-Amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-3-(hydroxymethyl)-4-pyridinyl]-2-(ethylamino)phenol

Product 1

HCID 1355304462-[6-Amino-4-[4-(ethylamino)-3-hydroxyphenyl]-5-(hydroxymethyl)-2-pyridinyl]-3-(cycloproylmethoxy)phenol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 5-[2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-3-(hydroxymethyl)-4-pyridinyl]-2-(ethylamino)phenol (0.013 g, 0.023 mmol) in 1,4-dioxane (0.5 mL) was added a solution of HCl in 1,4-dioxane (4N, 1.0 mL). After being stirred overnight, the mixture was diluted with diethyl ether. The resulting precipitate was collected by filtration under argon atmosphere, washed with Et2O, and dried under reduced pressure to give 2-[6-amino-4-[4-(ethylamino)-3-hydroxyphenyl]-5-(hydroxymethyl)-2-pyridinyl]-3-(cycloproylmethoxy)phenol. (0.008 g, 76%); LC-MS (m/z=422 M+1)

Workup

  1. filtrationThe resulting precipitate was collected by filtration under argon atmosphere
  2. washwashed with Et2O
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-f3518b89d4ac42228c6244ad731d5802
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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