Triethylsilane → HCID 118272364, compound

HRID 590862Notes

Reaction equation

HRID 590862 reaction equation
[C:1]1([C@H:7]([NH:9][C:10]([NH:12][C:13]2[N:18]=[CH:17][C:16]3[C:19]([NH:41][CH2:42][C:43]4[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=4)=[N:20][N:21](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:15]=3[CH:14]=2)=[O:11])[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]([NH:12][C:13]2[N:18]=[CH:17][C:16]3[C:19]([NH:41][CH2:42][C:43]4[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=4)=[N:20][NH:21][C:15]=3[CH:14]=2)=[O:11])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 118272473HCID 118272473, compound

Product 1

HCID 118272364HCID 118272364, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-1-(1-phenylethyl)-3-(3-((pyridin-3-ylmethyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (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 preparative HPLC to afford (R)-1-(1-phenylethyl)-3-(3-((pyridin-3-ylmethyl)amino)-1H-pyrazolo[4,3-c]pyridin-6-yl)urea. TFA (16.7 mg, 0.033 mmol, 59.5% yield) as a white solid. MS ESI calc'd. For C21H22N2O [M+H]+ 388. found 388. 1H NMR (ppm, 600 MHz, DMSO): δ 8.81 (s, 1H); 8.70 (s, 1H); 8.58 (d, J=5.0 Hz, 1H); 8.09 (s, 1H); 7.96 (s, 1H); 7.62 (s, 1H); 7.31-7.32 (m, 4H); 7.21 (t, J=6.6 Hz, 1H); 7.05 (s, 1H); 4.84 (t, J=7.2 Hz, 1H); 4.52 (s, 2H); 1.40 (d, J=7.0 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-f46961a4e44f4757bf2081ccbcedd4c1
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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