3-(Hydroxymethyl)-5-(pentafluoro-lambda6-sulphanyl)benzoic acid → 3-(Hydroxymethyl)-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055726Notes

Reaction equation

HRID 1055726 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.[OH:23][CH2:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([S:34]([F:39])([F:38])([F:37])([F:36])[F:35])[CH:33]=1)[C:28](O)=[O:29]>>[OH:23][CH2:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([S:34]([F:39])([F:35])([F:36])([F:37])[F:38])[CH:33]=1)[C:28]([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:29]

Participants

3

Reactant 2

HCID 896999933-(Hydroxymethyl)-5-(pentafluoro-lambda6-sulphanyl)benzoic acidHCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

Product 1

HCID 897003623-(Hydroxymethyl)-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

Procedure

62 mg (0.21 mmol) of the compound of Example 6A and 60 mg (0.21 mmol) of the compound of Example 37A were reacted and worked up analogously to the procedure of Example 16. The product obtained in this manner was re-purified 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 40 mg (48% of theory) of the title compound.

Workup

  1. customThe product obtained in this manner
  2. customwas re-purified by preparative HPLC (Method 15)
  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-f25326cf514641d49d56d0330931f73a
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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