Triethylsilane → HCID 73505444, compound

HRID 590860Notes

Reaction equation

HRID 590860 reaction equation
[CH2:1]([O:3][C:4](=[O:46])[NH:5][C:6]1[C:10]2[CH:11]=[N:12][C:13]([NH:15][C:16]([NH:18][C@@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])=[O:17])=[CH:14][C:9]=2[N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:7]=1)[CH3:2].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4](=[O:46])[NH:5][C:6]1[C:10]2[CH:11]=[N:12][C:13]([NH:15][C:16]([NH:18][C@@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])=[O:17])=[CH:14][C:9]=2[NH:8][N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 118649739HCID 118649739, compound

Product 1

HCID 73505444HCID 73505444, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-ethyl(6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate (0.037 mmol) was taken up in TFA (1 ml) and the reaction mixture stirred at room temperature for 1 h. Triethylsilane (0.006 ml, 0.037 mmol) was added drop wise, and the reaction mixture stirred for an additional 5 minutes. The mixture was concentrated, re-dissolved in DMSO (1.5 mL) and submitted for purification by mass-triggered preparative HPLC to afford (R)-ethyl(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate (5.7 mg, 0.015 mmol, 41.7% yield) as a white solid. MS ESI calc'd. For C18H21N6O3 [M+H]+ 369. found 369. 1H NMR (ppm, 600 MHz, DMSO): δ 8.95 (s, 1H); 7.78 (s, 1H); 7.42 (s, 1H); 7.30-7.31 (m, 4H); 7.19-7.22 (m, 1H); 4.85 (t, J=7.2 Hz, 1H); 4.14 (q, J=7.1 Hz, 2H); 1.39 (d, J=7.0 Hz, 3H); 1.22 (t, J=7.1 Hz, 3H).

Workup

  1. stirringthe reaction mixture stirred for an additional 5 minutes
  2. concentrationThe mixture was concentrated
  3. dissolutionre-dissolved in DMSO (1.5 mL)
  4. customsubmitted for purification by mass-triggered preparative HPLC

Sources & evidence

ORD record
ord-9e35f62a765b43359c407c8be976213f
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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