5-Bromo-N-[5-[2-methoxy-6-[(4-methoxyphenyl)methoxy]phenyl]-1H-pyrazol-3-yl]-2-pyrazinamine → 2-(3-(5-Bromopyrazin-2-ylamino)-1H-pyrazol-5-yl)-3-methoxyphenol

HRID 1878311Notes

Reaction equation

HRID 1878311 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9]2[CH:13]=[C:12]([C:14]3[C:19]([O:20]CC4C=CC(OC)=CC=4)=[CH:18][CH:17]=[CH:16][C:15]=3[O:30][CH3:31])[NH:11][N:10]=2)=[N:6][CH:7]=1>CO>[Br:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9]2[CH:13]=[C:12]([C:14]3[C:15]([O:30][CH3:31])=[CH:16][CH:17]=[CH:18][C:19]=3[OH:20])[NH:11][N:10]=2)=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 866543895-Bromo-N-[5-[2-methoxy-6-[(4-methoxyphenyl)methoxy]phenyl]-1H-pyrazol-3-yl]-2-pyrazinamine

Product 1

HCID 1363378112-(3-(5-Bromopyrazin-2-ylamino)-1H-pyrazol-5-yl)-3-methoxyphenolYield 64.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-N-(5-(2-methoxy-6-(4-methoxybenzyloxy)phenyl)-1H-pyrazol-3-yl)pyrazin-2-amine (3.1 g, 6.43 mmol) is dissolved in MeOH (100 mL). HCl gas is bubbled through the reaction mixture for 20 min. The mixture is stirred for 2 h and solvent is removed under reduced pressure. The residue is redissolved in 3:1 chloroform/isopropanol (100 mL) and combined with saturated NaHCO3 solution (100 mL). The layers are separated and the aqueous layer is extracted with ethyl acetate (3×50 mL). The combined organic layers are concentrated and triturated with methanol to give 1.5 g (64%) of a brown solid.

Workup

  1. customHCl gas is bubbled through the reaction mixture for 20 min
  2. customsolvent is removed under reduced pressure
  3. dissolutionThe residue is redissolved in 3:1 chloroform/isopropanol (100 mL)
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with ethyl acetate (3×50 mL)
  6. concentrationThe combined organic layers are concentrated
  7. customtriturated with methanol

Sources & evidence

ORD record
ord-9f71139fe382447b81a1c76c5c7f0eaa
Source dataset
uspto-grants-2012_11
Patent number
US08314108B2

Reaction notes

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