Trifluoroacetic acid → HCID 117843191, compound

HRID 2209088Notes

Reaction equation

HRID 2209088 reaction equation
[C:1](O)([C:3](F)(F)F)=[O:2].[F:8][CH:9]([F:42])[N:10]1[C:14]2[C:15]([O:33][C@@H:34]([C@H:36]3[CH2:40][NH:39][C:38](=[O:41])[CH2:37]3)[CH3:35])=[N:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[C:21]([O:31][CH3:32])[CH:20]=3)=[CH:18][C:13]=2[N:12]=[CH:11]1.C(N(CC)CC)C.C(OC(=O)C)(=O)C>C(Cl)Cl.CCOC(C)=O.O.[Cl-].[Na+].O>[C:1]([N:28]1[CH2:29][CH2:30][N:25]([C:22]2[CH:23]=[CH:24][C:19]([C:17]3[N:16]=[C:15]([O:33][C@@H:34]([C@H:36]4[CH2:40][NH:39][C:38](=[O:41])[CH2:37]4)[CH3:35])[C:14]4[N:10]([CH:9]([F:8])[F:42])[CH:11]=[N:12][C:13]=4[CH:18]=3)=[CH:20][C:21]=2[O:31][CH3:32])[CH2:26][CH2:27]1)(=[O:2])[CH3:3]

Participants

9

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 117843101HCID 117843101, compound

Product 1

HCID 117843191HCID 117843191, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The crude TFA salt of (R)-4-((R)-1-((3-(difluoromethyl)-6-(3-methoxy-4-(piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one: 3.67 (0.064 mmol) was dissolved in DCM (1 mL) and triethylamine (70 μL, 0.5 mmol) was added followed by acetic anhydride (7.5 μL, 0.079 mmol). The reaction mixture was stirred for 1.5 h and was diluted with EtOAc, water and brine. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (0-15% MeOH in DCM) to provide (R)-4-((R)-1-((6-(4-(4-acetylpiperazin-1-yl)-3-methoxyphenyl)-3-(difluoromethyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (3.69).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography (0-15% MeOH in DCM)

Sources & evidence

ORD record
ord-2cba5370f16a415e8a486bfa74beb8e7
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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