Hydrochloric Acid → 3-Ethyl-6-methoxy-5-[2-methoxy4-(trifluoromethoxy)phenyl]pyrazin-2-ylamine

HRID 349184Notes

Reaction equation

HRID 349184 reaction equation
Cl.[CH2:2]([C:4]1[C:5]([NH:25]CC2C=CC(OC)=CC=2)=[N:6][C:7]([O:23][CH3:24])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][C:11]=2[O:21][CH3:22])[N:9]=1)[CH3:3]>CCOCC.[Pd].CO>[CH2:2]([C:4]1[C:5]([NH2:25])=[N:6][C:7]([O:23][CH3:24])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:18])([F:19])[F:20])=[CH:12][C:11]=2[O:21][CH3:22])[N:9]=1)[CH3:3]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 22248943{3-Ethyl-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazin-2-yl} [(4-methoxyphenyl)methyl]amine

Product 1

HCID 222488983-Ethyl-6-methoxy-5-[2-methoxy4-(trifluoromethoxy)phenyl]pyrazin-2-ylamineYield 93.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1M hydrochloric acid in ether (2 mL) and 10% palladium on carbon (40 mg) are added to {3-ethyl-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazin-2-yl}[(4-methoxyphenyl)methyl]amine (115 mg, 0.25 mmol) in methanol (3 mL) under a nitrogen atmosphere. The mixture is then hydrogenated at 1 ATM for 18 hours, filtered through Celite and evaporated to give 3-ethyl-6-methoxy-5-[2-methoxy-4(trifluoromethoxy)phenyl]pyrazin-2-ylamine (80 mg).

Workup

  1. filtrationfiltered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-1833e10179654bc8b528b4344393e123
Source dataset
uspto-grants-2007_02
Patent number
US07179807B2

Reaction notes

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