Hydrochloric Acid → 1-(3-tert-Butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-cyclopropylmethoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone hydrochloride

HRID 658021Notes

Reaction equation

HRID 658021 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([C:12]([NH2:15])=[N:13][N:14]=3)[N:11]=2)[CH2:3][CH2:2]1.Br[CH2:17][C:18]([C:20]1[CH:25]=[C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:23]([O:32][CH3:33])=[C:22]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:21]=1)=[O:19].[ClH:38]>CN(C=O)C>[ClH:38].[C:34]([C:22]1[CH:21]=[C:20]([C:18](=[O:19])[CH2:17][N:13]2[C:12](=[NH:15])[N:10]3[N:11]=[C:6]([O:5][CH2:4][CH:1]4[CH2:2][CH2:3]4)[CH:7]=[CH:8][C:9]3=[N:14]2)[CH:25]=[C:24]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[C:23]=1[O:32][CH3:33])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 229297822-Bromo-1-(3-tert-butyl-4-methoxy-5-morpholinophenyl)ethanoneHCID 581369646-Cyclopropylmethoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

Product 1

HCID 669416281-(3-tert-Butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-cyclopropylmethoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-Cyclopropylmethoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W1.009; 350 mg) was initially charged in DMF (5 ml) at RT while stirring, and 2-bromo-1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)ethanone (O1.003; 631 mg) predissolved in DMF (5 ml) was added dropwise. 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 product was taken up with a little acetonitrile, diluted with water and, after addition of 2 eq. of HCl, freeze-dried. 500 mg of the title compound were obtained. LC-MS rt: 1.37 min [M+H]+: 495.2 (met. a)

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred at RT for 14 h
  3. customThen the solvent was removed under reduced pressure
  4. customthe residue was purified
  5. customsilica gel (40 g cartridge, dichloromethane/ethanol gradient of 0-40% in 60 min)
  6. additiondiluted with water
  7. customfreeze-dried

Sources & evidence

ORD record
ord-ac8981b43f524291aedbd489867b120c
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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