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

HRID 889875Notes

Reaction equation

HRID 889875 reaction equation
[CH2:1]([C:3]1[C:4]([NH:24]CC2C=CC(OC)=CC=2)=[N:5][C:6]([O:22][CH3:23])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[O:20][CH3:21])[N:8]=1)[CH3:2].Cl>CO.CCOCC.[Pd]>[CH2:1]([C:3]1[C:4]([NH2:24])=[N:5][C:6]([O:22][CH3:23])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:17])([F:18])[F:19])=[CH:11][C:10]=2[O:20][CH3:21])[N:8]=1)[CH3:2]

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

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 is added 1 M hydrochloric acid in ether (2 mL) and 10% palladium on carbon (40 mg). The mixture is then hydrogenated at 1 ATM for 18 h, 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-c2fb7ee559574fbda5642878b646a0d4
Source dataset
uspto-grants-2006_02
Patent number
US06995161B2

Reaction notes

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