Hydrochloric Acid → HCID 68870497, compound

HRID 2374863Notes

Reaction equation

HRID 2374863 reaction equation
CSC1N=NC(C(NC(=O)OC(C)(C)C)C)=CN=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([NH:31][C:32]2[N:33]=[N:34][C:35]([CH:38]([NH:40]C(=O)OC(C)(C)C)[CH3:39])=[CH:36][N:37]=2)[CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28].[ClH:48]>CO.O1CCOCC1>[ClH:48].[NH2:40][CH:38]([C:35]1[N:34]=[N:33][C:32]([NH:31][C:23]2[CH:22]=[C:21]([O:20][CH3:19])[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=2)=[N:37][CH:36]=1)[CH3:39]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 58711925HCID 58711925, compoundHCID 58711973HCID 58711973, compound

Product 1

HCID 68870497HCID 68870497, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 1-[3-(methylthio)-1,2,4-triazin-6-yl]ethylcarbamate (Intermediate 8) (1.2 g, 3.1 mmol) in methanol (10 mL) was added 4N HCl in dioxane (10 mL). After stirring for 30 minutes the volatiles were removed under reduced pressure to provide 6-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine hydrochloride as a foam. The foam was dissolved in methanol, ammonium hydroxide was added to neutralize the acid, and silica gel (5 g) was added followed by evaporation of the volatiles under reduced pressure. The pre-adsorbed solids were loaded into a solid loading cartridge and subjected to an isocratic elution using dichloromethane: methanol: ammonium hydroxide (95:4:1) using a RediSep silica gel cartridge (40 g; ISCO). The appropriate fractions were combined and concentrated under reduced pressure to give 6-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine (680 mg) as a yellow solid. 1H NMR (CDCl3): δ8.42 (s, 1H), 7.38 (s, 1H), 6.97 (s, 2H), 4.38 (d, J=7.0 Hz, 1H), 3.90 (s, 6H), 3.84 (s, 3H), 1.62 (br, 2H), 1.52 (d, J=7.0 Hz, 3H), 1.43 (s, 9H). MS m/z 306 (M+1).

Workup

  1. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-1c5e9725d5e743599e3ac6f78700e6e1
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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