Sodium Hydroxide → HCID 89699945, compound

HRID 1055739Notes

Reaction equation

HRID 1055739 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.[C:23]([C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([Cl:36])[N:35]=1)[C:30](O)=[O:31])([CH3:26])([CH3:25])[CH3:24].[OH-].[Na+]>>[C:23]([C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([Cl:36])[N:35]=1)[C:30]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([N:9]2[C:16]3[N:12]([N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:11]=[CH:10]2)[CH:4]=1)=[O:31])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 438405834-Pyridinecarboxylic acid, 2-chloro-6-(1,1-dimethylethyl)-HCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

Product 1

HCID 89699945HCID 89699945, compound

Procedure

50 mg (0.17 mmol) of the compound of Example 6A and 37 mg (0.17 mmol) of the compound of Example 43A were reacted analogously to the procedure of Example 15, except that here only 6 ml of 0.1 M aqueous sodium hydroxide solution (instead of 15 ml) were used for work-up. The product obtained was re-purified by preparative HPLC (column: Reprosil-Pur C18, 10 μm, 250 mm×30 mm; mobile phase: methanol/water with 0.05% TFA, with gradient). 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 44 mg (97% pure, 51% of theory) of the title compound.

Workup

  1. customThe product obtained
  2. customwas re-purified by preparative HPLC (column: Reprosil-Pur C18, 10 μm, 250 mm×30 mm; mobile phase: methanol/water with 0.05% TFA, with gradient)
  3. concentrationconcentrated under reduced pressure
  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

Sources & evidence

ORD record
ord-17d260bf6054468a8a1d1d4b87f8bc4b
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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