Acetonitrile → HCID 178494203, compound

HRID 1775195Notes

Reaction equation

HRID 1775195 reaction equation
C(OC(=O)[N:7]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:26]2[C:34]3[C:33](Cl)=[N:32][CH:31]=[N:30][C:29]=3[NH:28][CH:27]=2)O)=[CH:20][N:19]=1)[CH2:8][C:9]1[C:10]([O:16][CH3:17])=[N:11][CH:12]=[C:13]([F:15])[CH:14]=1)(C)(C)C.FC(F)(F)C(O)=[O:40].C([SiH](CC)CC)C.C(#N)C>O>[F:15][C:13]1[CH:14]=[C:9]([CH2:8][NH:7][C:18]2[N:19]=[CH:20][C:21]([CH2:24][C:26]3[C:34]4[C:33]([OH:40])=[N:32][CH:31]=[N:30][C:29]=4[NH:28][CH:27]=3)=[CH:22][CH:23]=2)[C:10]([O:16][CH3:17])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57963227HCID 57963227, compound

Product 1

HCID 178494203HCID 178494203, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

{5-[(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-hydroxy-methyl]-pyridin-2-yl}-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (78, 0.022 g, 0.043 mmol), trifluoroacetic acid (0.062 mL, 0.80 mmol), triethylsilane (0.15 mL, 0.97 mmol) and 0.46 mL acetonitrile were combined in a round bottom flask. The reaction was heated at reflux for 3 hours, then poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with methanol in dichloromethane. Appropriate fractions were combined and solvents removed under vacuum to provide the desired compound (P-0099, 0.0072 g). MS (ESI) [M+H+]+=380.8.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel column chromatography
  9. washeluting with methanol in dichloromethane
  10. customsolvents removed under vacuum

Sources & evidence

ORD record
ord-2b63467a845f4c0cb419d9cd5225408f
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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