Triethylsilane → HCID 118272013, compound

HRID 588197Notes

Reaction equation

HRID 588197 reaction equation
[CH2:1]([S:3][C:4]1[C:8]2[CH:9]=[N:10][C:11]([NH:13][C:14]([NH:16][C@@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])=[O:15])=[CH:12][C:7]=2[N:6](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:5]=1)[CH3:2].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([S:3][C:4]1[C:8]2[CH:9]=[N:10][C:11]([NH:13][C:14]([NH:16][C@@H:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH3:18])=[O:15])=[CH:12][C:7]=2[NH:6][N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 118272174HCID 118272174, compound

Product 1

HCID 118272013HCID 118272013, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-1-(3-(Ethylthio)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (40.6 mg, 0.070 mmol) was dissolved in TFA (1 mL) and triethylsilane (0.017 mL, 0.104 mmol) was added. The reaction mixture stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo, diluted with DMSO (1 mL), filtered, and purified by mass-triggered reverse phase HPLC. The fractions containing pure product were concentrated in vacuo to give (R)-1-(3-(ethylthio)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea, which was obtained as the trifluoroacetic acid salt. MS ESI calc'd. For C17H19N5OS [M+1]+ 342. found 342. 1H NMR (500 MHz, DMSO-d6) δ 13.13 (s, 1H), 9.09 (s, 1H), 8.65 (s, 1H), 7.73 (s, 1H), 7.61 (s, 1H), 7.33 (d, J=4.4 Hz, 4H), 7.22 (dt, J=4.1, 8.6 Hz, 1H), 4.94-4.77 (m, 1H), 3.10 (q, J=7.3 Hz, 2H), 1.39 (d, J=7.0 Hz, 3H), 1.27 (t, J=7.3 Hz, 3H). Examples 80-81 (Table 13) were prepared according to Scheme 8 following similar procedures described for Example 79 using the appropriate sodium thiol, which can be achieved by those of ordinary skill in the art of organic synthesis. Example 81 was obtained as the trifluoroacetic acid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with DMSO (1 mL)
  3. filtrationfiltered
  4. custompurified by mass-triggered reverse phase HPLC
  5. additionThe fractions containing pure product
  6. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-0b702ebbfcae486cb413e5ce6fe5e6ba
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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