HCID 89699639, compound → HCID 89699845, compound

HRID 1055728Notes

Reaction equation

HRID 1055728 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N:9]1[C:16]2[N:12]([N:13]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=2)[CH:11]=[CH:10]1.FC(F)(F)C(O)=O.[F:30][S:31]([F:50])([F:49])([F:48])([F:47])[C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([CH2:41][N:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)[CH:40]=1)[C:35](O)=[O:36]>>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:35](=[O:36])[C:34]2[CH:38]=[C:39]([CH2:41][N:42]3[CH2:46][CH2:45][CH2:44][CH2:43]3)[CH:40]=[C:32]([S:31]([F:50])([F:49])([F:48])([F:30])[F:47])[CH:33]=2)=[CH:4][C:3]=1[N:9]1[C:16]2[N:12]([N:13]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=2)[CH:11]=[CH:10]1

Participants

3

Reactant 2

HCID 89699639HCID 89699639, compoundHCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

Product 1

HCID 89699845HCID 89699845, compound

Procedure

45 mg (0.16 mmol) of the compound of Example 6A and 70 mg (0.16 mmol) of the compound of Example 38A were reacted analogously to the procedure of Example 16, except that here the reaction was, after the reaction had ended, directly separated into its components by preparative HPLC (Method 15). The product-containing fractions were combined and concentrated under reduced pressure, 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 gave 48 mg (51% of theory) of the title compound.

Workup

  1. customdirectly separated into its components by preparative HPLC (Method 15)
  2. concentrationconcentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed successively with saturated potassium carbonate solution and saturated sodium chloride solution
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customDrying of the residue

Sources & evidence

ORD record
ord-7a3e435d311c43dd9f843e41da8bdac9
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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