2-Methoxybenzylamine → HCID 10018173, compound

HRID 1744226Notes

Reaction equation

HRID 1744226 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][NH2:15].CCN(C(C)C)C(C)C>CN1CCCC1>[Br:8][C:6]1[N:7]=[C:2]([NH:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[O:11][CH3:10])[C:3]([NH2:9])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 812922-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 6200042-Amino-3,5-dibromopyrazine

Product 1

HCID 10018173HCID 10018173, compound

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1.00 eq. of (2) is dissolved in N-methylpyrrolidine (2 mL) at room temperature. To this solution is added 3.00 eq. of 2-methoxybenzyl amine and 0.4 mL Hunig's Base. The resulting solution is heated to 90° C. and stirred for 12–24 hours under nitrogen. The resulting mixture is partitioned between ethyl acetate and H2O. The aqueous layer is extracted twice with ethyl acetate and the combined organic extracts are dried over Na2SO4. The solvent is removed under reduced pressure and the resulting residue is purified via flash chromatography to provide (4).

Workup

  1. customThe resulting mixture is partitioned between ethyl acetate and H2O
  2. extractionThe aqueous layer is extracted twice with ethyl acetate
  3. dry with materialthe combined organic extracts are dried over Na2SO4
  4. customThe solvent is removed under reduced pressure
  5. customthe resulting residue is purified via flash chromatography

Sources & evidence

ORD record
ord-2f073245b172403fb1142cf6fec7d2a9
Source dataset
uspto-grants-2006_03
Patent number
US07015227B2

Reaction notes

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