Diisopropylethylamine → HCID 58298321, compound

HRID 1525510Notes

Reaction equation

HRID 1525510 reaction equation
BrC1C=C(C)C2NC(NC)=NC=2C=1.[Br:14][C:15]1[CH:16]=[C:17]([CH3:33])[C:18]2[N:22]=[C:21]([NH:23][CH3:24])[N:20]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:19]=2[CH:32]=1.C(N(C(C)C)CC)(C)C.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CN(C)C=O>[Br:14][C:15]1[CH:16]=[C:17]([CH3:33])[C:18]2[N:22]=[C:21]([NH:23][CH3:24])[N:20]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[C:19]=2[CH:32]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 178482309HCID 178482309, compound

Product 1

HCID 58298321HCID 58298321, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 6-bromo-4-methyl-2-(methylamino)-1H-benzo[d]imidazole-1-carboxylate (6-Bromo-4-methylbenzimidazol-2-yl)-N-methylamine (0.128 g, 0.533 mmol), diisopropylethylamine (0.464 mL, 2.67 mmol), di-tert-butyl dicarbonate (0.349 g, 1.599 mmol) and N,N-dimethylformamide (5 mL) were combined in a 100 mL round bottom flask, capped and stirred at room temperature for 21 h. The resulting mixture was partitioned between water and ethyl acetate. The layers were separated and the organics were washed with water and brine. The organics were dried over magnesium sulfate, filtered, concentrated under reduced pressure and purified using flash chromatography (10-30% ethyl acetate in hexanes) to give the desired product (0.092 g, 0.27 mmol, 51% yield) as a yellow waxy solid. MS (ESI) m/z 340 [M]+, 342 [M+2]+.

Workup

  1. customcapped
  2. customThe resulting mixture was partitioned between water and ethyl acetate
  3. customThe layers were separated
  4. washthe organics were washed with water and brine
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified

Sources & evidence

ORD record
ord-a2402f68b09641b7b5e55720faa85cee
Source dataset
uspto-grants-2015_07
Patent number
US09079900B2

Reaction notes

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