Trifluoroacetic acid → HCID 59593320, compound

HRID 1754667Notes

Reaction equation

HRID 1754667 reaction equation
C(OC(=O)[N:7]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[C:10]([O:25][CH3:26])[N:9]=1)(C)(C)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[C:23]4[C:18](=[N:19][CH:20]=[CH:21][CH:22]=4)[NH:17][CH:16]=3)=[C:10]([O:25][CH3:26])[N:9]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59593308HCID 59593308, compound

Product 1

HCID 59593320HCID 59593320, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (4-Chloro-benzyl)-5-[hydroxy-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-6-methoxy-pyridin-2-yl-carbamic acid tert-butyl ester (68, 40.0 mg, 0.081 mmol) in acetonitrile (10.0 mL) were added trifluoroacetic acid (0.30 mL, 0.0039 mol) and triethylsilane (0.60 mL, 0.0038 mol). The reaction was heated to reflux for 3 hours. The reaction was concentrated to remove the solvents, then purified with silica gel column chromatography eluting with 40% ethyl acetate in hexane to give compound (P-0081, 10 mg, 32.7%). MS (ESI) [M+H+]+=379.4.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe reaction was concentrated
  4. customto remove the solvents
  5. custompurified with silica gel column chromatography
  6. washeluting with 40% ethyl acetate in hexane
  7. customto give compound (P-0081, 10 mg, 32.7%)

Sources & evidence

ORD record
ord-2d8d14957d5a4102bd354b3c5a394ccf
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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