Hydrochloric Acid → 6-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine

HRID 2374967Notes

Reaction equation

HRID 2374967 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:11]=[N:12][C:13]([CH:16]([NH:18]C(=O)OC(C)(C)C)[CH3:17])=[CH:14][N:15]=2)=[CH:5][CH:4]=1.Cl>C(O)C>[NH2:18][CH:16]([C:13]1[N:12]=[N:11][C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:15][CH:14]=1)[CH3:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 587119581,1-Dimethylethyl [1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]carbamate2×

Product 1

HCID 587119996-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amineYield 79.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1,1-dimethylethyl [1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]carbamate (Intermediate 46) (3.00 g, 8.69 mmol) in ethanol saturated with hydrogen chloride (30 mL) was stirred overnight at room temperature. The resulting mixture was reduced under vacuum, partitioned between ethyl acetate and saturated sodium bicarbonate solution and the mixture filtered to give a solid residue. The aqueous layer was re-extracted with ethyl acetate (5×) and the combined organic layers dried with magnesium sulfate, filtered and reduced under vacuum. The residue was purified by chromatography on silica gel eluting with 50% ethyl acetate in petrol to afford a solid which was combined with the initial solid to give 6-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine (1.70 g) as a yellow solid. 1H NMR (CDCl3): δ8.35 (s, 1H), 7.53 (d, J=9.0 Hz, 2H), 7.34 (s, 1H), 6.92 (d, J=9.0 Hz, 2H), 4.33 (q, J=6.7 Hz, 1H), 3.82 (s, 3H), 1.51 (d, J=6.7 Hz, 3H).

Workup

  1. custompartitioned between ethyl acetate and saturated sodium bicarbonate solution
  2. filtrationthe mixture filtered
  3. customto give a solid residue
  4. extractionThe aqueous layer was re-extracted with ethyl acetate (5×)
  5. dry with materialthe combined organic layers dried with magnesium sulfate
  6. filtrationfiltered
  7. customThe residue was purified by chromatography on silica gel eluting with 50% ethyl acetate in petrol
  8. customto afford a solid which

Sources & evidence

ORD record
ord-1118202f769d454c89d24f3adde12f56
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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