N-(1,1'-Biphenyl-4-yl)-N'-[3-({2-{(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]ethoxy}methyl)phenyl]urea → N-(1,1'-Biphenyl-4-yl)-N'-{3-[(2-{[6-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}ethoxy)methyl]phenyl}urea acetate

HRID 503052Notes

Reaction equation

HRID 503052 reaction equation
[C:1]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][CH2:29][C@@H:30]([C:32]3[CH:43]=[CH:42][C:35]4[O:36][C:37](C)([CH3:40])[O:38][CH2:39][C:34]=4[CH:33]=3)[OH:31])[CH:12]=2)=[O:9])=[CH:3][CH:2]=1>C(O)(=O)C.O>[C:37]([OH:38])(=[O:36])[CH3:40].[C:1]1([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:2]=[CH:3][C:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][CH2:29][C@H:30]([OH:31])[C:32]3[CH:43]=[CH:42][C:35]([OH:36])=[C:34]([CH2:39][OH:38])[CH:33]=3)[CH:12]=2)=[O:9])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 66844972N-(1,1'-Biphenyl-4-yl)-N'-[3-({2-{(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]ethoxy}methyl)phenyl]urea

Product 1

HCID 66846216N-(1,1'-Biphenyl-4-yl)-N'-{3-[(2-{[6-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)hexyl]oxy}ethoxy)methyl]phenyl}urea acetateYield 211.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of N-(1,1′-biphenyl-4-yl)-N′-[3-({2-[(6-{[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]ethoxy}methyl)phenyl]urea (0.089 g) in acetic acid (4 ml) and water (2 ml) were stirred under nitrogen at 70° C. for 30 min. The reaction mixture was cooled to room temperature before concentrating under vacuum and azeotroping with MeOH (2×10 ml) to give the title compound (0.097 g). LCMS RT=3.08 min, ES+ve 628 (MH)+.

Workup

  1. concentrationbefore concentrating under vacuum
  2. customazeotroping with MeOH (2×10 ml)

Sources & evidence

ORD record
ord-470d7eba45ec4fd7b50abfb79014d0b3
Source dataset
uspto-grants-2010_08
Patent number
US07776895B2

Reaction notes

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