Triethylsilane → HCID 178471185, compound

HRID 571418Notes

Reaction equation

HRID 571418 reaction equation
[CH2:1]([NH:8][C:9](=[O:46])[NH:10][C:11]1[N:16]=[CH:15][C:14]2[C:17]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[N:18][N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:13]=2[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([NH:8][C:9](=[O:46])[NH:10][C:11]1[N:16]=[CH:15][C:14]2[C:17]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[N:18][NH:19][C:13]=2[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 89525900ethyl 3-(6-(3-benzylureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)propanoate

Product 1

HCID 178471185HCID 178471185, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of ethyl 3-(6-(3-benzylureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)propanoate (38.7 mg, 0.063 mmol) in TFA (1 ml) was charged with triethylsilane (12 μl, 0.075 mmol) and stirred at RT for 2 hr. LCMS shows conversion to the desired mass. Purified via mass-triggered reverse-phase HPLC to provide ethyl 3-(6-(3-benzylureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)propanoate (8.4 mg, 0.017 mmol, 27.5% yield) as a white solid (TFA salt). MS ESI calc'd for C19H21N5O3 [M+H]+=368, found 368. 1H NMR (500 MHz, DMSO-d6) δ 9.53 (br s, 1H), 8.85 (s, 1H), 7.85 (s, 1H), 7.51 (s, 1H), 7.32 (m, 4H), 7.25 (m, 1H), 4.36 (d, J=5.9 Hz, 2H), 4.02 (q, J=7.1 Hz, 2H), 3.17 (t, J=7.3 Hz, 2H), 2.79 (t, J=7.3 Hz, 2H), 1.13 (t, J=7.1 Hz, 3H).

Workup

  1. customPurified via mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-c7ad2f8e415b4177923d914d169413be
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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