Trifluoroacetic acid → HCID 57619311, compound

HRID 1367371Notes

Reaction equation

HRID 1367371 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, compound

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-53518b556cc8407eb24f05b5dc73b2fd
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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