Trifluoroacetic acid → HCID 178488773, compound

HRID 253480Notes

Reaction equation

HRID 253480 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]2[NH:6][C:7]([CH2:9][O:10][C:11]3[C:16]([O:17][CH3:18])=[CH:15][C:14]([CH:19]([C:21]4[C:29]5[C:24](=[N:25][CH:26]=[C:27]([CH3:30])[CH:28]=5)[NH:23][CH:22]=4)O)=[C:13]([F:31])[CH:12]=3)=[N:8][C:4]=2[CH:3]=1.ClC1C=CC2NC(COC3C=C(F)C(C(OC)C4C5C(=NC=C(C)C=5)NC=4)=CC=3OC)=NC=2C=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]2[NH:6][C:7]([CH2:9][O:10][C:11]3[CH:12]=[C:13]([F:31])[C:14]([CH2:19][C:21]4[C:29]5[C:24](=[N:25][CH:26]=[C:27]([CH3:30])[CH:28]=5)[NH:23][CH:22]=4)=[CH:15][C:16]=3[O:17][CH3:18])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 178492500HCID 178492500, compoundHCID 178492554HCID 178492554, compound

Product 1

HCID 178488773HCID 178488773, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

[4-(5-chloro-1H-benzoimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-phenyl]-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (228a) and 5-chloro-2-{5-fluoro-2-methoxy-4-[methoxy-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenoxymethyl}-1H-benzoimidazole (228b) were dissolved in acetonitrile. Triethylsilane was added followed by trifluoroacetic acid. The reaction was stirred for one hour at 60° C. The solvent was removed under reduced pressure, Ethyl acetate was added and the organic layer was washed with sodium bicarbonate saturated solution and brine, then dried over anhydrous sodium sulfate and concentrated. Purification with silica gel column chromatography, eluting with a gradient of methanol (2-25%) in dichloromethane, provided the desired compound P-2184. MS (ESI): [M+H+]+=451.0, [M−H+]−=449.1.

Workup

  1. customThe solvent was removed under reduced pressure, Ethyl acetate
  2. additionwas added
  3. washthe organic layer was washed with sodium bicarbonate saturated solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customPurification with silica gel column chromatography
  7. washeluting with a gradient of methanol (2-25%) in dichloromethane

Sources & evidence

ORD record
ord-2aac62a3c0d044a3be998d8d48d186d8
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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