Triethylsilane → (R)-1-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

HRID 588177Notes

Reaction equation

HRID 588177 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[CH:8]=[N:9][C:10]([NH:12][C:13]([NH:15][C@@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])=[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-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]1[C:7]2[CH:8]=[N:9][C:10]([NH:12][C:13]([NH:15][C@@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])=[O:14])=[CH:11][C:6]=2[NH:5][N:4]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 118271885(R)-1-(3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Product 1

HCID 118272029(R)-1-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-1-(3-Methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (156 mg, 0.282 mmol) and triethylsilane (0.068 mL, 0.423 mmol) were stirred in TFA (2 mL) at room temperature for 2 h. Saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by flash chromatography (0-15% MeOH-EtOAc) gave (R)-1-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. For C16H17N5O2 [M+1]+ 312. found 312. 1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.93 (s, 1H), 8.54 (s, 1H), 7.76 (br s, 1H), 7.48 (s, 1H), 7.35-7.31 (m, 4H), 7.25-7.20 (m, 1H), 4.88-4.83 (m, 1H), 3.96 (s, 3H), 1.39 (d, J=6.5 Hz, 3H).

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography (0-15% MeOH-EtOAc)

Sources & evidence

ORD record
ord-04c804731a7a46d3bfda3fe79f9a3ca8
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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