Acetic Anhydride → HCID 68426174, compound

HRID 642410Notes

Reaction equation

HRID 642410 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:22])=[C:8]2[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:22][C:23](=[O:25])[CH3:24])=[C:8]2[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68428543HCID 68428543, compound

Product 1

HCID 68426174HCID 68426174, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-cyano-4-hydroxy-1-(3-methyl-butyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (0.4 g, 1.33 mmol), example 97(a), and acetic anhydride (0.25 mL, 2.65 mmol) in methylene chloride (8 mL) at ambient temperature was added triethylamine (0.37 mL, 2.65 mmol). The reaction mixture was stirred at ambient temperature for 2.5 h before 100 mL of methylene chloride was added. The organic solution was washed with 80 mL of water, dried, filtered, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-50% ethyl acetate in hexanes to produce 0.44 g of a colorless oil. MS: (+) m/z 344.3 (M+1).

Workup

  1. additionwas added
  2. washThe organic solution was washed with 80 mL of water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography
  7. washeluting from silica gel with a gradient of 0-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-46c9f5cc4e46451db0c2522380d80f79
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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