N-(3-{6-[1-(4-Methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methyl-phenyl)-3-(4-methylpiperazin-1-yl)-5-(pentafluoro-lambda6-sulphanyl)benzamide → 3-(4-Methylpiperazin-1-yl)-N-{4-methyl-3-[6-(1H-pyrazol-4-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]-phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055703Notes

Reaction equation

HRID 1055703 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]4[N:20]([C:21]5[CH:22]=[C:23]([NH:28][C:29](=[O:49])[C:30]6[CH:35]=[C:34]([S:36]([F:41])([F:40])([F:39])([F:38])[F:37])[CH:33]=[C:32]([N:42]7[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]7)[CH:31]=6)[CH:24]=[CH:25][C:26]=5[CH3:27])[CH:19]=[CH:18][N:16]4[N:17]=3)[CH:10]=[N:9]2)=CC=1>FC(F)(F)C(O)=O>[CH3:48][N:45]1[CH2:46][CH2:47][N:42]([C:32]2[CH:31]=[C:30]([CH:35]=[C:34]([S:36]([F:41])([F:38])([F:37])([F:39])[F:40])[CH:33]=2)[C:29]([NH:28][C:23]2[CH:24]=[CH:25][C:26]([CH3:27])=[C:21]([N:20]3[C:15]4[N:16]([N:17]=[C:13]([C:11]5[CH:10]=[N:9][NH:8][CH:12]=5)[CH:14]=4)[CH:18]=[CH:19]3)[CH:22]=2)=[O:49])[CH2:43][CH2:44]1

Participants

3

Reactant 1

HCID 89699916N-(3-{6-[1-(4-Methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methyl-phenyl)-3-(4-methylpiperazin-1-yl)-5-(pentafluoro-lambda6-sulphanyl)benzamide

Product 1

HCID 1366302453-(4-Methylpiperazin-1-yl)-N-{4-methyl-3-[6-(1H-pyrazol-4-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]-phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

At 80° C., 90 mg (0.12 mmol) of the compound of Example 48A were stirred in 0.61 ml of trifluoroacetic acid for 3 h. The reaction was then concentrated and the residue was purified by preparative HPLC (Method 18). The product fractions were concentrated, and the residue was dissolved in ethyl acetate and washed successively with saturated potassium carbonate solution and saturated sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. Drying of the residue under high vacuum gave 40 mg (53% of theory) of the title compound.

Workup

  1. concentrationThe reaction was then concentrated
  2. customthe residue was purified by preparative HPLC (Method 18)
  3. concentrationThe product fractions were concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed successively with saturated potassium carbonate solution and saturated sodium chloride solution
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customDrying of the residue under high vacuum

Sources & evidence

ORD record
ord-e0d1b8d4bccd43ed93c9ced54555c752
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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