Trifluoroacetic acid → HCID 59593320, compound

HRID 2261577Notes

Reaction equation

HRID 2261577 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-d07c52ffaeef4d45a5310fab106d85b6
Source dataset
uspto-grants-2010_12
Patent number
US07846941B2

Reaction notes

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