HCID 68663028, compound → HCID 59293729, compound

HRID 2370380Notes

Reaction equation

HRID 2370380 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](COCC)([CH3:10])[N:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[CH:19]=1>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([C:15]([CH3:17])([CH3:16])[CH3:18])[C:6]=2[CH:19]=1

Participants

3

Reactant 1

HCID 68663028HCID 68663028, compound

Product 1

HCID 59293729HCID 59293729, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 6-bromo-1-tert-butyl-2-ethoxymethyl-2-methyl-2,3-dihydro-1H-benzoimidazole (Step 25.2) (2.04 g, 6.51 mmol) and TFA (10 ml) is stirred at it overnight, quenched by addition of a saturated solution of NaHCO3 (100 mL) and extracted with EtOAc (2×150 mL). The organic phase is washed with a saturated solution of NaHCO3 (2×50 mL), dried (Na2SO4), filtered and concentrated. The residue purified by silica gel column chromatography (DCM/MeOH, 1:0→98:2) to afford 1.05 g of the title compound as a white solid: ESI-MS: 267.0/269.0 [M+H]+; tR=2.99 min (System 1); TLC: Rf=0.58 (DCM/MeOH, 9:1).

Workup

  1. customquenched by addition of a saturated solution of NaHCO3 (100 mL)
  2. extractionextracted with EtOAc (2×150 mL)
  3. washThe organic phase is washed with a saturated solution of NaHCO3 (2×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue purified by silica gel column chromatography (DCM/MeOH, 1:0→98:2)

Sources & evidence

ORD record
ord-3555b4a5aa57438e933e7a105a0ebb78
Source dataset
uspto-grants-2014_04
Patent number
US08710085B2

Reaction notes

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