Ammonia → HCID 178427388, compound

HRID 74453Notes

Reaction equation

HRID 74453 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[N:11]=[C:12]([CH3:14])[NH:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23](Br)[CH:22]=2)=[O:18].[I-:39].[Na+].CN[C@@H]1CCCC[C@H]1NC.N>[Cu]I.O1CCOCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23]([I:39])[CH:22]=2)=[O:18]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 5238Sodium IodideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 68004804[5-amino-1-(2-methyl-3H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone

Product 1

HCID 178427388HCID 178427388, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
108.5 °C

Procedure

A mixture consisting of [5-amino-1-(2-methyl-3H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone (1 g), copper (I) iodide (161 mg), sodium iodide (508 mg), trans-N,N′-dimethylcyclohexane-1,2-diamine (267 μl), and anhydrous dioxane (5 ml) was stirred in a pressure-proof container at 105 to 112° C. under a nitrogen atmosphere for 20 hours. The reaction mixture was poured into an aqueous solution of 2 M ammonia, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methanol/dichloromethane=0/100 to 20/100) to give [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[6-iodo-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone (0.67 g, 62%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe desiccant was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (methanol/dichloromethane=0/100 to 20/100)

Sources & evidence

ORD record
ord-afd8b636136f4b44bb057c2ff6f34363
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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