Trifluoroacetic acid → HCID 178494910, compound

HRID 571388Notes

Reaction equation

HRID 571388 reaction equation
[CH3:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]1[C:10]2[CH:11]=[N:12][C:13]([NH:15][C:16]([NH:18][C@@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])=[O:17])=[CH:14][C:9]=2[N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.C([SiH](CC)CC)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:10]2[CH:11]=[N:12][C:13]([NH:15][C:16]([NH:18][C@@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])=[O:17])=[CH:14][C:9]=2[NH:8][N:7]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117601640(R,E)-1-(3-(3-methoxyprop-1-en-1-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Product 1

HCID 178494910HCID 178494910, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 12052TriethylsilaneSolvent2×

Procedure

To the solution of crude (R,E)-1-(3-(3-methoxyprop-1-en-1-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (142 mg, 0.239 mmol) in DCM (0.8 mL) TFA (0.3 mL) and triethylsilane (0.1 mL) were added. The mixture was stirred at room temperature for 30 min and additional TFA (0.5 mL) and triethylsilane (0.3 mL) were added. The mixture was stirred at room temperature for 30 min, evaporated in vacuo and purified by MS-directed reverse phase preparative-HPLC (C-18 stationary phase, eluting with a H2O/MeCN gradient with 0.1% TFA), to afford (R)-1-(3-(3-methoxypropyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (21.7 mg, 0.046 mmol, 19%). MS ESI calc'd. for C19H24N5O2 [M+H]+ 354, found 354. 1H NMR (600 MHz, DMSO-d6) δ 12.92 (s, 1H), 9.38 (s, 1H), 8.80 (s, 1H), 7.88 (s, 1H), 7.46 (s, 1H), 7.38-7.15 (m, 5H), 4.85 (m, 1H), 3.33 (t, J=6.3 Hz, 2H), 3.19 (s, 3H), 2.91 (t, J=7.6 Hz, 2H), 1.99-1.85 (m, 2H), 1.39 (d, J=6.9 Hz, 3H),

Workup

  1. stirringThe mixture was stirred at room temperature for 30 min
  2. customevaporated in vacuo
  3. custompurified by MS-directed reverse phase preparative-HPLC (C-18 stationary phase
  4. washeluting with a H2O/MeCN gradient with 0.1% TFA),

Sources & evidence

ORD record
ord-e31952d1db7e4437b785f29eb73d5628
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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