Triethylsilane → 1-(3-(methylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(phenyl(tetrahydrofuran-2-yl)methyl)urea

HRID 590854Notes

Reaction equation

HRID 590854 reaction equation
[CH3:1][NH:2][C:3]1[C:7]2[CH:8]=[N:9][C:10]([NH:12][C:13]([NH:15][CH:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:17]3[CH2:21][CH2:20][CH2:19][O:18]3)=[O:14])=[CH:11][C:6]=2[N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:4]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH3:1][NH:2][C:3]1[C:7]2[CH:8]=[N:9][C:10]([NH:12][C:13]([NH:15][CH:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:17]3[CH2:21][CH2:20][CH2:19][O:18]3)=[O:14])=[CH:11][C:6]=2[NH:5][N:4]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 1182722511-(3-(methylamino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(phenyl(tetrahydrofuran-2-yl)methyl)urea

Product 1

HCID 1182720281-(3-(methylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(phenyl(tetrahydrofuran-2-yl)methyl)urea

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-(3-(methylamino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(phenyl(tetrahydrofuran-2-yl)methyl)urea (320 mg, 0.526 mmol) was taken up in TFA (3.0 ml). Triethylsilane (0.126 ml, 0.789 mmol) was added and the reaction was allowed to stir at rt for 30 mins. The reaction mixture was concentrated in vacuo. Saturated NaHCO3 was slowly added. The products were then washed with EtOAc (3×). The combined organic layers were then washed with brine, dried over MgSO4, filtered through celite, then concentrated in vacuo. The oil was taken up in 2 ml of DCM and loaded directly onto silica gel. Purification by MPLC 0-15% EtOAc/MeOH gave 1-(3-(methylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(phenyl(tetrahydrofuran-2-yl)methyl)urea. MS ESI calc'd. for C19H23N6O2 [M+H]+ 367. found 367.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionSaturated NaHCO3 was slowly added
  3. washThe products were then washed with EtOAc (3×)
  4. washThe combined organic layers were then washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered through celite
  7. concentrationconcentrated in vacuo
  8. customPurification by MPLC 0-15% EtOAc/MeOH

Sources & evidence

ORD record
ord-36281cb62a234136be12ae82381a5b3b
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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