N-(3-{[({3-[(2-[(6-({(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy}ethoxy)methyl]phenyl}amino)carbonyl]amino)-phenyl)pyridine-3-carboxamide → N-(3-{[({3-[(2-{[6-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]-ethyl}amino)hexyl]oxy}ethoxy)methyl]phenyl}amino)carbonyl]amino}phenyl)-pyridine-3-carboxamide

HRID 1014828Notes

Reaction equation

HRID 1014828 reaction equation
CC1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:51])[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:27]=[C:28]([NH:32][C:33]([NH:35][C:36]4[CH:37]=[C:38]([NH:42][C:43]([C:45]5[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=5)=[O:44])[CH:39]=[CH:40][CH:41]=4)=[O:34])[CH:29]=[CH:30][CH:31]=3)=[CH:11][C:5]=2[CH2:4][O:3]1>C(O)(=O)C.O>[OH:51][C@H:12]([C:10]1[CH:9]=[CH:8][C:6]([OH:7])=[C:5]([CH2:4][OH:3])[CH:11]=1)[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:27]=[C:28]([NH:32][C:33]([NH:35][C:36]2[CH:37]=[C:38]([NH:42][C:43]([C:45]3[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=3)=[O:44])[CH:39]=[CH:40][CH:41]=2)=[O:34])[CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 66844859N-(3-{[({3-[(2-[(6-({(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy}ethoxy)methyl]phenyl}amino)carbonyl]amino)-phenyl)pyridine-3-carboxamide

Product 1

HCID 10146481N-(3-{[({3-[(2-{[6-({(2R)-2-Hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]-ethyl}amino)hexyl]oxy}ethoxy)methyl]phenyl}amino)carbonyl]amino}phenyl)-pyridine-3-carboxamideYield 86.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of N-(3-{[({3-[(2-[(6-({(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy}ethoxy)methyl]phenyl}amino)carbonyl]amino)-phenyl)pyridine-3-carboxamide (0.109 g) in acetic acid (4 ml) and water (2 ml) was heated to 68° for 30 min. The mixture was cooled to room temperature before concentrating in vacuo to leave a residue that was purified by Biotage. Elution with dichloromethane-EtOH-ammonia (25:8:1) followed by solvent evaporation in vacuo gave the title compound (0.089 g). LCMS RT=2.02 min, ES+ve 672 (MH)+.

Workup

  1. concentrationbefore concentrating in vacuo
  2. customto leave a residue that
  3. customwas purified by Biotage
  4. washElution with dichloromethane-EtOH-ammonia (25:8:1)
  5. customfollowed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-5e57b532bca040238958e9477311226e
Source dataset
uspto-grants-2011_07
Patent number
US07982067B2

Reaction notes

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