Hydrochloric Acid → HCID 66941426, compound

HRID 1524615Notes

Reaction equation

HRID 1524615 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:13]([NH2:16])=[N:14][N:15]=2)[N:12]=1)[CH2:4][CH3:5])[CH3:2].Br[CH2:18][C:19]([C:21]1[CH:26]=[C:25](OCC)[CH:24]=[C:23]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:22]=1C)=[O:20].[C:35](#N)[CH3:36].[ClH:38].CN([CH:42]=[O:43])C>>[ClH:38].[C:30]([C:23]1[CH:22]=[C:21]([C:19](=[O:20])[CH2:18][N:14]2[C:13](=[NH:16])[N:11]3[N:12]=[C:7]([O:6][CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:8]=[CH:9][C:10]3=[N:15]2)[CH:26]=[C:25]([CH2:42][O:43][CH2:35][CH3:36])[CH:24]=1)([CH3:31])([CH3:32])[CH3:33]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 6342AcetonitrileHCID 66941231HCID 66941231, compoundHCID 86650815HCID 86650815, compound

Product 1

HCID 66941426HCID 66941426, compound

Procedure

6-(1-Ethylpropoxy)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W1.008; 205 mg) was initially charged in DMF (5 ml) at RT while stirring, and 2-bromo-1-(3-tert-butyl-5-ethoxy-methylphenyl)ethanone (O1.008; 290 mg) was added dropwise predissolved in DMF (5 ml). The reaction mixture was stirred at RT for 14 h. Then the solvent was removed under reduced pressure and the residue was purified using silica gel (40 g cartridge, dichloromethane/ethanol gradient of 0-40% in 60 min). The still contaminated product was subsequently purified by means of preparative HPLC. The clean product fractions were combined, freed of the acetonitrile under reduced pressure and freeze-dried. The residue was dissolved in water and acetonitrile and, after addition of 3 eq. of HCl, freeze-dried. 72 mg of the title compound were obtained.

Workup

  1. stirringThe reaction mixture was stirred at RT for 14 h
  2. customThen the solvent was removed under reduced pressure
  3. customthe residue was purified
  4. customsilica gel (40 g cartridge, dichloromethane/ethanol gradient of 0-40% in 60 min)
  5. customThe still contaminated product was subsequently purified by means of preparative HPLC
  6. customfreeze-dried
  7. dissolutionThe residue was dissolved in water
  8. customfreeze-dried

Sources & evidence

ORD record
ord-383d226abdf9469d87edf28af8b792d0
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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