3-tert-Butyl-N-(3-{6-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methylphenyl)-5-(4-methylpiperazin-1-yl)benzamide → 3-tert-Butyl-5-(4-methylpiperazin-1-yl)-N-{4-methyl-3-[6-(1H-pyrazol-4-yl)-1H-imidazo[1,2-b]-pyrazol-1-yl]phenyl}benzamide

HRID 1055707Notes

Reaction equation

HRID 1055707 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:40]=[C:41]([N:43]2[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]2)[CH:42]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N:18]2[C:25]3[N:21]([N:22]=[C:23]([C:26]4[CH:27]=[N:28][N:29](CC5C=CC(OC)=CC=5)[CH:30]=4)[CH:24]=3)[CH:20]=[CH:19]2)[CH:12]=1)=[O:9])([CH3:4])([CH3:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:40]=[C:41]([N:43]2[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]2)[CH:42]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N:18]2[C:25]3[N:21]([N:22]=[C:23]([C:26]4[CH:27]=[N:28][NH:29][CH:30]=4)[CH:24]=3)[CH:20]=[CH:19]2)[CH:12]=1)=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 896997983-tert-Butyl-N-(3-{6-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methylphenyl)-5-(4-methylpiperazin-1-yl)benzamide

Product 1

HCID 1366302363-tert-Butyl-5-(4-methylpiperazin-1-yl)-N-{4-methyl-3-[6-(1H-pyrazol-4-yl)-1H-imidazo[1,2-b]-pyrazol-1-yl]phenyl}benzamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

68 mg (76% pure, 79 μmol) of the compound of Example 57A were initially charged in 0.32 ml of trifluoroacetic acid and stirred at 80° C. for 3 h. The mixture was then purified directly by preparative HPLC (Method 29). The product fractions were concentrated under reduced pressure and the residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. This gave 41 mg (97% of theory) of the title compound.

Workup

  1. customThe mixture was then purified directly by preparative HPLC (Method 29)
  2. concentrationThe product fractions were concentrated under reduced pressure
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-012239db16a44644a3e87568688e4e11
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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