Triethylsilane → HCID 73505651, compound

HRID 590866Notes

Reaction equation

HRID 590866 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[C:11]2[CH:12]=[N:13][C:14]([NH:16][C:17]([NH:19][C@@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])=[O:18])=[CH:15][C:10]=2[N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:8]=1)=[O:5].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[C:11]2[CH:12]=[N:13][C:14]([NH:16][C:17]([NH:19][C@@H:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH3:21])=[O:18])=[CH:15][C:10]=2[NH:9][N:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 118271847HCID 118271847, compound

Product 1

HCID 73505651HCID 73505651, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-2-methoxy-N-(6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide (0.056 mmol) was taken up in TFA (1 ml) and the reaction mixture was stirred at room temperature for 1 h. Triethylsilane (0.009 ml, 0.056 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 prep. HPLC to afford (R)-2-methoxy-N-(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide. TFA (15.9 mg, 0.033 mmol, 58.9% yield) as a white solid. MS ESI calc'd. For C18H21N6O3 [M+H]+ 369. found 369. 1H NMR (ppm, 600 MHz, DMSO): δ 10.62 (s, 1H); 9.28 (br s, 1H); 9.00 (s, 1H); 7.75 (s, 1H); 7.46 (s, 1H); 7.31-7.32 (m, 4H); 7.19-7.22 (m, 1H); 4.85 (t, J=7.2 Hz, 1H); 4.09 (s, 2H); 3.35 (s, 3H); 1.39 (d, J=6.9 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 prep

Sources & evidence

ORD record
ord-5b055cdfdf514daca0d5f45748185caa
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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