Triethylamine → HCID 66673692, compound

HRID 423408Notes

Reaction equation

HRID 423408 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([NH2:19])[CH2:15]2)=[N:12][CH:13]=1.C(N(CC)CC)C>ClCCl>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([NH:19][C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH2:15]2)=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 53629854HCID 53629854, compound

Product 1

HCID 66673692HCID 66673692, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methoxyacetyl chloride (208 μL, 2.27 mmol) to a 0° C. solution of (R)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-ylamine (0.5 g, 2.07 mmol) and triethylamine (317 μL, 2.27 mmol) in dichloromethane (10 mL). Remove the ice bath and stir the reaction overnight. Wash the reaction mixture with 10% aqueous NaHSO4 (20 mL). Separate the organic portion and extract the aqueous portion with dichloromethane (2×10 mL). Dry the combined organics over Na2SO4, filter, and concentrate to dryness. Purify using chromatography (0 to 5% MeOH/CH2Cl2) to afford 525 mg (81%) of the title compound. LC-MS/ES m/z (79Br) 314.0 [M+H]+.

Workup

  1. customRemove the ice bath
  2. customthe reaction overnight
  3. washWash the reaction mixture with 10% aqueous NaHSO4 (20 mL)
  4. customSeparate the organic portion
  5. extractionextract the aqueous portion with dichloromethane (2×10 mL)
  6. dry with materialDry the combined organics over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate to dryness
  9. customPurify

Sources & evidence

ORD record
ord-cc72645cbedd453496ab3db020188ceb
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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