Triethylamine → 2-[5-Bromo-4-(1,1,3,3-tetramethylbutylamino)-6-oxopyridazin-1(6H)-yl]-N-(pyridin-4-ylmethyl)acetamide

HRID 2092071Notes

Reaction equation

HRID 2092071 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH2:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[O:12])[C:6](=[O:9])[C:7]=1[Br:8].C([N:23]([CH2:26][CH3:27])CC)C.CC(N)(C[CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])C.O1CCOC[CH2:39]1.O>>[Br:8][C:7]1[C:6](=[O:9])[N:5]([CH2:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[O:12])[N:4]=[CH:3][C:2]=1[NH:23][C:26]([CH3:27])([CH3:39])[CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 177765132,5,5-Trimethylhexan-2-amineHCID 218864351,4-Dioxane--water (1/1)HCID 595743872-(4,5-Dibromo-6-oxopyridazin-1(6H)-yl)-N-(pyridin-4-ylmethyl)acetamide

Product 1

HCID 595743762-[5-Bromo-4-(1,1,3,3-tetramethylbutylamino)-6-oxopyridazin-1(6H)-yl]-N-(pyridin-4-ylmethyl)acetamideYield 25%

Procedure

2-(4,5-Dibromo-6-oxopyridazin-1(6H)-yl)-N-(pyridin-4-ylmethyl)acetamide (50 mg, 124 μmol) in dioxane-water (1:1, 2 mL) was stirred with triethylamine (52 μL, 372 μmol) and 2,5,5-trimethylhexan-2-amine (16 mg, 112 μmol) at 90° C. for 26 hours. After completion of the reaction, the solvent was removed by vacuum distillation, and the residue was mixed with saturated aqueous sodium chloride and extracted with chloroform three times. The combined organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by vacuum distillation. The resulting residue was purified by silica gel chromatography (chloroform/methanol=10/1) to give the desired product (13 mg, 25% yield).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by vacuum distillation
  3. additionthe residue was mixed with saturated aqueous sodium chloride
  4. extractionextracted with chloroform three times
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by vacuum distillation
  7. customThe resulting residue was purified by silica gel chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-6e9ef58306234159a76720ed54d5fd8b
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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