Sodium Hydroxide → N-{2-Hydroxy-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055745Notes

Reaction equation

HRID 1055745 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:15]3[N:11]([N:12]=[C:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[CH:14]=3)[CH:10]=[CH:9]2)[C:3]=1[OH:22].[F:23][S:24]([F:37])([F:36])([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](O)=[O:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[OH-].[Na+]>CN(C=O)C.O>[OH:22][C:3]1[C:4]([N:8]2[C:15]3[N:11]([N:12]=[C:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[CH:14]=3)[CH:10]=[CH:9]2)=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][CH:33]=[C:25]([S:24]([F:37])([F:23])([F:34])([F:35])[F:36])[CH:26]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 27792093-(Pentafluorosulfanyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896999202-Amino-6-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenol

Product 1

HCID 86690984N-{2-Hydroxy-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(pentafluoro-lambda6-sulphanyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

80 mg (0.192 mmol) of the compound of Example 71A and 48 mg (0.192 mmol) of 3-(pentafluoro-λ6-sulphanyl)benzoic acid were dissolved in 1.5 ml anhydrous DMF, and 88 mg (0.231 mmol) of HATU and 40 μl (0.231 mmol) of N,N-diisopropylethylamine were added in succession. The reaction mixture was stirred at RT for 30 min and then stirred into about 10 ml of water. The resulting precipitate was filtered off with suction and dissolved in 3 ml of methanol, and 385 μl (0.385 mmol) of 1 M aqueous sodium hydroxide solution were added. The mixture was then stirred at RT for 30 min and then, by preparative HPLC, separated completely into its components (Method 33). The product fractions were combined and freed from the solvent. The residue was triturated with a mixture of 5 ml of pentane and 1 ml of dichloromethane at RT. Filtration with suction and drying of the solid under high vacuum gave 32 mg (32% of theory) of the title compound.

Workup

  1. filtrationThe resulting precipitate was filtered off with suction
  2. dissolutiondissolved in 3 ml of methanol
  3. stirringThe mixture was then stirred at RT for 30 min
  4. customby preparative HPLC, separated completely into its components (Method 33)
  5. customThe residue was triturated with a mixture of 5 ml of pentane and 1 ml of dichloromethane at RT
  6. filtrationFiltration with suction
  7. customdrying of the solid under high vacuum

Sources & evidence

ORD record
ord-35a4da84df834a8caeaa6ac0b1889f92
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

Loading…