Dimethylamine → HCID 10136850, compound

HRID 2183503Notes

Reaction equation

HRID 2183503 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8]([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)=[CH:7][N:6]=[N:5]1.[NH:30]([CH3:32])[CH3:31]>CN(C=O)C>[CH3:31][N:30]([CH2:2][CH2:3][N:4]1[C:8]([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)=[CH:7][N:6]=[N:5]1)[CH3:32]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 131724937HCID 131724937, compound

Product 1

HCID 10136850HCID 10136850, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-({[1-(2-bromoethyl)-1H-1,2,3-triazol-5-yl}methyl}oxy)-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (125 mg, 0.27 mmol) in DMF (5 ml) and Me2NH (2.0 M in THF, 4 ml, 8 mmol) were heated at 80° C. for 4 h in a sealed tube. The reaction mixture was concentrated under reduced pressure and then taken up in MeOH/CH2Cl2 and dry loaded onto silica. The mixture was purified by column chromatography on silica using 1.5% MeOH/CH2Cl2 containing 1% NH3 as eluent to yield the desired phthalazine (50 mg, 44%). 1H NMR (360 MHz, CDCl3) δ 8.69 (1H, d, J=8.0 Hz), 8.18 (1H, d, J=8.0 Hz), 8.07 (1H, s), 7.98 (1H, t, J=7.6 Hz), 7.82 (1H, t, J=7.6 Hz), 6.85 (1H, s), 5.86 (2H, s), 4.66 (2H, t, J=6.9 Hz), 2.92 (2H, m), 2.59 (3H, s), 2.32 (6H, s). m/z (ES+) 420 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customdry
  3. customThe mixture was purified by column chromatography on silica using 1.5% MeOH/CH2Cl2 containing 1% NH3 as eluent

Sources & evidence

ORD record
ord-d7bf63cc097d4ffdbd385966d836babb
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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