Benzamide → N-(2-(4-(isopropylsulfonyl)phenyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)benzamide

HRID 68658Notes

Reaction equation

HRID 68658 reaction equation
CNCCNC.I[C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[N:15]=2)[N:10]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:9]=1.[C:39]([NH2:47])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[CH:26]([S:23]([C:20]1[CH:21]=[CH:22][C:17]([C:14]2[N:15]=[C:16]3[C:8]([NH:47][C:39](=[O:46])[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:9][N:10]([S:29]([C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=4)(=[O:31])=[O:30])[C:11]3=[N:12][CH:13]=2)=[CH:18][CH:19]=1)(=[O:24])=[O:25])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 2331BenzamideHCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 667631397-Iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine

Product 1

HCID 71143663N-(2-(4-(isopropylsulfonyl)phenyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)benzamideYield 37.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
95 °C

Procedure

CuI (95 mg, 0.4988 mmol), and N,N′-dimethylethane-1,2-diamine (176 mg, 1.997 mmol) in dioxane (5 mL) was heated for 5 minutes at 100° C. in a microwave. 1 mL of this solution was added to a mixture of 7-iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine (100 mg, 0.1720 mmol), benzamide (104.2 mg, 0.8600 mmol) and K3PO4 (73.02 mg, 0.344 mmol) in dioxane (1 mL) and the solution was heated at 95° C. for 1 hour. The reaction mixture is concentrated in vacuo. The residue was partitioned between DCM and water. Combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo yielding an oil which was purified by prep HPLC to give the sub-title product (37 mg, 37%). MS (ES+) 575.1.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. dry with materialCombined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customyielding an oil which
  7. customwas purified by prep HPLC

Sources & evidence

ORD record
ord-c9d1960d0ea24e88ab301818a7fa4b81
Source dataset
uspto-grants-2014_09
Patent number
US08822469B2

Reaction notes

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