1,4-Dioxane → HCID 178427333, compound

HRID 513871Notes

Reaction equation

HRID 513871 reaction equation
O1CCOCC1.C(=O)(O)[O-].[Na+].[NH2:12][C:13]1[N:17]([C:18]2[CH:27]=[CH:26][C:21]3[NH:22][C:23]([CH3:25])=[N:24][C:20]=3[CH:19]=2)[N:16]=[CH:15][C:14]=1[C:28]([C:30]1[N:31]([S:36]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH:32]=[C:33](Br)[CH:34]=1)=[O:29].[C:46]1(B(O)O)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>O>[NH2:12][C:13]1[N:17]([C:18]2[CH:27]=[CH:26][C:21]3[NH:22][C:23]([CH3:25])=[N:24][C:20]=3[CH:19]=2)[N:16]=[CH:15][C:14]=1[C:28]([C:30]1[N:31]([S:36]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH:32]=[C:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:34]=1)=[O:29]

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 178427317[5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[4-bromo-1-(toluene-4-sulfonyl)-1H-pyrrol-2-yl]-methanone

Product 1

HCID 178427333HCID 178427333, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dioxane (1.5 ml) and an aqueous solution (1.5 ml) of 1 M sodium bicarbonate were added to [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[4-bromo-1-(toluene-4-sulfonyl)-1H-pyrrol-2-yl]-methanone (57 mg), palladium chloride bis-triphenylphosphine complex (10 mg), and phenylboronic acid (37 mg). The mixture was reacted at 140° C. in a microwave reactor for ten minutes. The reaction mixture was diluted with water (5 ml), and then extracted with ethyl acetate. The organic layers were combined, and concentrated under reduced pressure. After HPLC purification, the eluate was desalted using PLHCO3 cartridge (PolymerLabs), and then concentrated under reduced pressure. Thus, [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[4-phenyl-1-(toluene-4-sulfonyl)-1H-pyrrol-2-yl]-methanone was obtained as a yellow powder (15 mg, 26%).

Workup

  1. customThe mixture was reacted at 140° C. in a microwave reactor for ten minutes
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customAfter HPLC purification
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5a03fbcc353c4131bd7ea2ba21ab9afa
Source dataset
uspto-grants-2015_08
Patent number
US09102692B2

Reaction notes

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