Water → N-{4-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(pentafluoro-lambda6-sulphanyl)-5-(piperazin-1-ylmethyl)benzamide

HRID 1055729Notes

Reaction equation

HRID 1055729 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([S:33]([F:38])([F:37])([F:36])([F:35])[F:34])[CH:32]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([N:16]2[C:23]3[N:19]([N:20]=[C:21]([C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH:22]=3)[CH:18]=[CH:17]2)[CH:10]=1)=[O:7])=O.[N:39]1(C(OC(C)(C)C)=O)[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl>[CH3:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:4]=[C:3]([CH2:1][N:39]3[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]3)[CH:32]=[C:31]([S:33]([F:38])([F:36])([F:34])([F:37])[F:35])[CH:30]=2)=[CH:10][C:11]=1[N:16]1[C:23]2[N:19]([N:20]=[C:21]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH:22]=2)[CH:18]=[CH:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 897000213-Formyl-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

Product 1

HCID 89699847N-{4-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(pentafluoro-lambda6-sulphanyl)-5-(piperazin-1-ylmethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90 mg (0.16 mmol) of the compound of Example 55A and 34 mg (0.18 mmol) of tert-butyl piperazine-1-carboxylate were dissolved in 3.2 ml of dichloromethane, 52 mg (0.25 mmol) of sodium triacetoxyborohydride were added and the mixture was stirred at RT for 3 h. 3 ml of water were then added, and the mixture was extracted with 6 ml of ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was then stirred in 2 ml of dichloromethane and 1 ml of trifluoroacetic acid at RT for 2 h. The reaction was then concentrated on a rotary evaporator and the residue was separated into its components by preparative HPLC (Method 24). The product-containing fractions were combined and concentrated under reduced pressure and the residue dried under high vacuum. This gave 11 mg (11% of theory) of the title compound.

Workup

  1. extractionthe mixture was extracted with 6 ml of ethyl acetate
  2. washThe organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. stirringThe residue was then stirred in 2 ml of dichloromethane
  7. wait1 ml of trifluoroacetic acid at RT for 2 h
  8. concentrationThe reaction was then concentrated on a rotary evaporator
  9. customthe residue was separated into its components by preparative HPLC (Method 24)
  10. concentrationconcentrated under reduced pressure
  11. customthe residue dried under high vacuum

Sources & evidence

ORD record
ord-8a08fba2e4924b7a89d44549012e540f
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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