Triethylsilane → HCID 73505442, compound

HRID 590856Notes

Reaction equation

HRID 590856 reaction equation
[CH2:1]([NH: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]([NH: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 118272478HCID 118272478, compound

Product 1

HCID 73505442HCID 73505442, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-1-(3-(3-ethylureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (0.046 mmol) was taken up in TFA (1 ml) and the reaction mixture stirred at room temperature for 1 h. Triethylsilane (0.008 ml, 0.046 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)-1-(3-(3-ethylureido)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. TFA (9.2 mg, 0.019 mmol, 41.2% yield) as a white solid. MS ESI calc'd. For C18H27N7O2 [M+H]+ 368. found 368. 1H NMR (ppm, 600 MHz, DMSO): δ 9.67 (s, 1H); 9.08 (s, 1H); 7.81 (s, 1H); 7.36 (s, 1H); 7.31-7.32 (m, 4H); 7.19-7.22 (m, 1H); 4.81-4.86 (m, 1H); 3.16-3.20 (m, 2H); 1.39 (d, J=7.0 Hz, 3H); 1.07 (t, J=7.2 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-80d73df435244317b2638becdd22ca0a
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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