3,4,5-Trimethoxyaniline → HCID 58711925, compound

HRID 2374862Notes

Reaction equation

HRID 2374862 reaction equation
CS([C:5]1[N:6]=[N:7][C:8]([CH:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])=[CH:9][N:10]=1)(=O)=O.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[NH2:26]>O1CCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:33][O:32][C:28]1[CH:27]=[C:25]([NH:26][C:5]2[N:6]=[N:7][C:8]([CH:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])=[CH:9][N:10]=2)[CH:24]=[C:23]([O:22][CH3:21])[C:29]=1[O:30][CH3:31]

Participants

5

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 58711940HCID 58711940, compound2×

Product 1

HCID 58711925HCID 58711925, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 1-[3-(methylsulfonyl)-1,2,4-triazin-6-yl]ethylcarbamate (Intermediate 7) (2.0 g, 6.5 mmol) in tetrahydrofuran (50 mL) was added 3,4,5-trimethoxyaniline (1.8 g, 9.7 mmol) and 4-toluenesulfonic acid monohydrate (60 mg). After stirring for 24 hours, silica gel (10 g) was added to the solution, followed by evaporation of the volatiles under reduced pressure. The pre-adsorbed solids were loaded into a solid loading cartridge and subjected to a gradient elution using ethyl acetate:hexane (20:80) to ethyl acetate:hexanes (50:50) using a RediSep silica gel cartridge (40 g; ISCO). The appropriate fractions were combined and concentrated under reduced pressure to give tert-butyl 1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethylcarbamate (1.3 g) as a white solid. 1H NMR (CDCl3): δ8.30 (s, 1H), 7.49 (br, 1H), 6.95 (s, 2H), 5.40-5.30 (m, 1H), 5.00-4.83 (m, 1H), 3.89 (s, 6H), 3.84 (s, 3H), 1.58 (d, J=7.0 Hz, 3H), 1.43 (s, 9H). MS m/z 406 (M+1).

Workup

  1. additionsilica gel (10 g) was added to the solution
  2. customfollowed by evaporation of the volatiles under reduced pressure
  3. washsubjected to a gradient elution
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-51e2a85853874d1288b9f94112bf78eb
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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