Methylamine → HCID 10201284, compound

HRID 2183524Notes

Reaction equation

HRID 2183524 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([CH2:9][O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]3=[N:21][N:22]=[C:23]([C:24]4[CH:28]=[C:27]([CH3:29])[O:26][N:25]=4)[N:13]3[N:12]=2)[N:6]=[N:5]1.[CH3:30][NH2:31]>C(O)C>[CH3:30][NH:31][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([CH2:9][O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]3=[N:21][N:22]=[C:23]([C:24]4[CH:28]=[C:27]([CH3:29])[O:26][N:25]=4)[N:13]3[N:12]=2)[N:6]=[N:5]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 131724948HCID 131724948, compound

Product 1

HCID 10201284HCID 10201284, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-[1-(2-bromoethyl)-1H-[1,2,3]triazol-4-ylmethoxy]-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (90 mg, 0.20 mmol), ethanol (2 ml) and methylamine (2.0 M in THF, 7.5 ml, 15 mmol) were heated at 90° C. for 4 h in a sealed tube. The reaction solvent was removed in vacuo, water added and extracted into dichloromethane. These extracts were washed with water and saturated brine then dried over magnesium sulphate, filtered and concentrated in vacuo. The resultant solid was purified by preparative thin layer chromatography on silica eluting with 5% methanol-dichloromethane containing 1% NH3 to give methyl-(2-{4-[3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazin-6-yloxymethyl]-[1,2,3]triazol-1-yl}ethyl)amine as a White solid (32 mg). 1H NMR (400 MHz, d6-DMSO) δ 2.25 (3H, s), 2.59 (3H, s), 2.91 (2H, t, J6), 4.43 (2H, t, J 6), 5.70 (2H, s), 7.18 (1H, s), 7.94 (1H, t, J 7), 8.10 (1H, t, J 7), 8.19 (1H, d, J 8), 8.46 (1H, s), 8.56 (1H, d, J 8). m/z (ES+) 406 (M+H+).

Workup

  1. customThe reaction solvent was removed in vacuo, water
  2. additionadded
  3. extractionextracted into dichloromethane
  4. washThese extracts were washed with water and saturated brine
  5. dry with materialthen dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant solid was purified by preparative thin layer chromatography on silica eluting with 5% methanol-dichloromethane containing 1% NH3

Sources & evidence

ORD record
ord-a11d1d2e4e0e4645bb78b064560f4383
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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