Trifluoroacetic acid → HCID 57619311, compound

HRID 1256795Notes

Reaction equation

HRID 1256795 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:28]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[CH3:29])[S:5][C:6]=1[CH:7]([C:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:11]([Si](C(C)C)(C(C)C)C(C)C)[CH:10]=1)[OH:8].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:28]([CH3:29])[C:4]2[S:5][C:6]([C:7]([C:9]3[C:17]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[NH:11][CH:10]=3)=[O:8])=[CH:2][N:3]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66971130HCID 66971130, compound

Product 1

HCID 57619311HCID 57619311, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of {4-chloro-2-[(4-chloro-benzyl)-methyl-amino]-thiazol-5-yl}-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (552, 1 g, 2 mmol), triethylsilane (2 mL, 12 mmol), and trifluoroacetic acid (1 mL, 13 mmol) in acetonitrile (10 mL) was stirred at 40° C. for 2 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with sodium bicarbonate and brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with methanol in dichloromethane to provide the desired compound as a yellow solid (P-0178, 0.17 g, 30%). MS (ESI) [M+H+]+=383.09.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with methanol in dichloromethane

Sources & evidence

ORD record
ord-9d3d99fc516d4244bfc6ca49fa1cb15e
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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