Trifluoroacetic acid → HCID 57619311, compound

HRID 1754739Notes

Reaction equation

HRID 1754739 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-a91cc55711fc41e6b9587c355b592521
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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