Trifluoroacetic acid → 5-[4-(Phenethylaminomethyl)phenoxy]pyrazine-2-carboxamide

HRID 492433Notes

Reaction equation

HRID 492433 reaction equation
C(OC(=O)[N:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[N:28][C:27]([C:30](=[O:32])[NH2:31])=[CH:26][N:25]=2)=[CH:19][CH:18]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH2:8]([NH:7][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[N:25]=[CH:26][C:27]([C:30]([NH2:31])=[O:32])=[N:28][CH:29]=2)=[CH:19][CH:18]=1)[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59730363[4-(5-Carbamoylpyrazin-2-yloxy)benzyl]phenethylcarbamic acid tert-butyl ester

Product 1

HCID 597301685-[4-(Phenethylaminomethyl)phenoxy]pyrazine-2-carboxamideYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve [4-(5-carbamoylpyrazin-2-yloxy)benzyl]phenethylcarbamic acid tert-butyl ester (0.015 g, 0.0334 mmol) in dichloromethane (1 mL). Add TFA (1 mL). Stir at room temperature for 6 hours. Load directly onto an SCX (5 g) column. Wash the column with methanol thien elute with 2.0 M NH3 in methanol to give the title compound (11.5 mg, 98%): MS ES+ 348.9 (M+H)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-95% over 19 min], tR=9.4 min, 98.4 purity.

Workup

  1. washWash the column with methanol
  2. washthien elute with 2.0 M NH3 in methanol

Sources & evidence

ORD record
ord-4223929f98ec454ba2f96ccdcf8f0b0e
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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