Hydrochloric Acid → HCID 66941426, compound

HRID 658022Notes

Reaction equation

HRID 658022 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-c24c4248a54a471f8a86601c455fa974
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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