HCID 53629212, compound → HCID 15952967, compound

HRID 1896479Notes

Reaction equation

HRID 1896479 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:13]([CH2:20][N:21]3[CH2:25][CH:24]([CH2:26][CH2:27][CH3:28])[CH2:23][C:22]3=[O:29])=[C:14]([C:16]([F:19])([F:18])[F:17])[N:15]=2)[N:12]=1>FC(F)(F)C(O)=O>[NH2:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:13]([CH2:20][N:21]3[CH2:25][CH:24]([CH2:26][CH2:27][CH3:28])[CH2:23][C:22]3=[O:29])=[C:14]([C:16]([F:18])([F:17])[F:19])[N:15]=2)[N:12]=1

Participants

3

Reactant 1

HCID 53629212HCID 53629212, compound

Product 1

HCID 15952967HCID 15952967, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-{[6-[(2,4-dimethoxybenzyl)amino]-2-(trifluoromethyl)imidazo[1,2-b]pyridazin-3-yl]methyl}-4-propylpyrrolidin-2-one x268 (396 mg, 0.83 mmol) is stirred at room temperature in trifluoroacetic acid until its complete consumption (17 hours). After TFA removal under reduced pressure, the residue is taken in saturated K2CO3 aqueous solution and extracted with ethyl acetate (3×15 ml). The cumulated organic layers are dried over MgSO4, filtered and condensed under reduced pressure to yield the crude material which is purified by reverse phase preparative chromatography (gradient acetonitrile/water/TFA) to afford 1-{[6-amino-2-(trifluoromethyl)imidazo[1,2-b]pyridazin-3-yl]methyl}-4-propylpyrrolidin-2-one 53.

Workup

  1. customAfter TFA removal under reduced pressure
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. dry with materialThe cumulated organic layers are dried over MgSO4
  4. filtrationfiltered
  5. customcondensed under reduced pressure
  6. customto yield the crude material which
  7. customis purified by reverse phase preparative chromatography (gradient acetonitrile/water/TFA)

Sources & evidence

ORD record
ord-a13643c8b63a4fa995a709ddb3c404a9
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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