Trifluoroacetic acid → 2-[4-(2-Aminoethyl)phenoxy]nicotinamide

HRID 228269Notes

Reaction equation

HRID 228269 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[C:22]([C:23](=[O:25])[NH2:24])=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[N:18]=[CH:19][CH:20]=[CH:21][C:22]=2[C:23]([NH2:24])=[O:25])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59729996{2-[4-(3-Carbamoylpyridin-2-yloxy)phenyl]ethyl}carbamic acid tert-butyl ester

Product 1

HCID 597303512-[4-(2-Aminoethyl)phenoxy]nicotinamideYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve {2-[4-(3-carbamoylpyridin-2-yloxy)phenyl]ethyl}carbamic acid tert-butyl ester (0.518 g, 1.45 mmol) in dichloromethane (8.4 mL). Add TFA (8.4 mL) and stir at room temperature for 4 hours. Concentrate the reaction mixture. Load the product onto an SCX column with methanol. Wash the column with methanol then elute with 50% (2.0 M NH3 in methanol) in methanol to give the title compound (0.38 g, 100%): TOF MS ES+ 258.1 (M+H)+, base peak TOF ES+ 241.1 (M-NH2)+, HRMS calcd for C14H16N3O2 258.1243 (M+H)+, found 258.1228, time 0.34 min; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 5-95% over 19 min], tR=13.4 min, 100% purity.

Workup

  1. concentrationConcentrate the reaction mixture
  2. washWash the column with methanol
  3. washthen elute with 50% (2.0 M NH3 in methanol) in methanol

Sources & evidence

ORD record
ord-c8c09f2008da46e1817bd3e9f3e68e07
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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