Acetic Anhydride → HCID 117843659, compound

HRID 2209078Notes

Reaction equation

HRID 2209078 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([O:23][C@@H:24]([C@H:26]3[CH2:30][NH:29][C:28](=[O:31])[CH2:27]3)[CH3:25])=[N:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)=[CH:13][N:12]=3)=[CH:10][C:5]=2[N:4]=[CH:3]1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>C(Cl)Cl>[C:32]([N:20]1[CH2:21][CH2:22][N:17]([C:14]2[CH:15]=[CH:16][C:11]([C:9]3[N:8]=[C:7]([O:23][C@@H:24]([C@H:26]4[CH2:30][NH:29][C:28](=[O:31])[CH2:27]4)[CH3:25])[C:6]4[N:2]([CH3:1])[CH:3]=[N:4][C:5]=4[CH:10]=3)=[N:12][CH:13]=2)[CH2:18][CH2:19]1)(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 117843325HCID 117843325, compound

Product 1

HCID 117843659HCID 117843659, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of (R)-4-((R)-1-((3-methyl-6-(5-(piperazin-1-yl)pyridin-2-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one 3.39 (50 mg, 0.119 mmol) and TEA (0.12 g) in DCM (2 mL) was added acetic anhydride (0.02 g, 0.18 mmol) at 0° C. The reaction mixture was warmed to rt and stirred for 2 h. Then the reaction mixture was extracted with ethyl acetate and washed with brine. After drying, the solvent was removed, the residue was purified by silica chromatographgy to provide 36 mg of (R)-4-((R)-1-((6-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-3-methyl-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one 3.40.

Workup

  1. extractionThen the reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. customAfter drying
  4. customthe solvent was removed
  5. customthe residue was purified by silica chromatographgy

Sources & evidence

ORD record
ord-e68114fa05244e1bb9e95dceeed9ed3f
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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