Triethylsilane → HCID 73505650, compound

HRID 590864Notes

Reaction equation

HRID 590864 reaction equation
[C:1]1([C@H:7]([NH:9][C:10](=[O:46])[NH:11][C:12]2[N:17]=[CH:16][C:15]3[C:18]([NH:40][C:41]([CH:43]4[CH2:45][CH2:44]4)=[O:42])=[N:19][N:20](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:14]=3[CH:13]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[C:1]1([C@H:7]([NH:9][C:10](=[O:46])[NH:11][C:12]2[N:17]=[CH:16][C:15]3[C:18]([NH:40][C:41]([CH:43]4[CH2:45][CH2:44]4)=[O:42])=[N:19][NH:20][C:14]=3[CH:13]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 118271704HCID 118271704, compound

Product 1

HCID 73505650HCID 73505650, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)—N-(6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxamide (0.037 mmol) was taken up in TFA (1 ml) and the reaction mixture was 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)—N-(6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxamide (4.3 mg, 0.012 mmol, 31.8% yield) as a white solid. MS ESI calc'd. For C19H21N6O2 [M+H]+ 365. found 365. 1H NMR (ppm, 600 MHz, DMSO): δ 11.15 (s, 1H); 9.33 (br s, 1H); 9.05 (s, 1H); 7.79 (br s, 1H); 7.41 (s, 1H); 7.31 (d, J=4.4 Hz, 4H); 7.21 (d, J=5.7 Hz, 1H); 4.84 (t, J=7.2 Hz, 1H); 1.93 (m, 1H); 1.38 (d, J=7.0 Hz, 3H); 0.83 (t, J=6.9 Hz, 4H).

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-335aa35d34924fd09a4d5c75e15d7fcd
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

Loading…