Trifluoroacetic acid → (R)-1-(3-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

HRID 571396Notes

Reaction equation

HRID 571396 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[N:14][C:15]([NH:17][C:18]([NH:20][C@@H:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH3:22])=[O:19])=[CH:16][C:11]=3[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH:13]=[N:14][C:15]([NH:17][C:18]([NH:20][C@@H:21]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH3:22])=[O:19])=[CH:16][C:11]=3[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 89525854(R)-1-(3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Product 1

HCID 71555466(R)-1-(3-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)ureaYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of (R)-1-(3-(4-fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (61 mg, 0.10 mmol) in DCM (0.5 mL) was added TFA (0.5 mL) and triethylsilane (0.05 mL, 0.313 mmol). The mixture was stirred at room temperature for 10 min, concentrated in vacuo and purified on reversed phase HPLC to afford (R)-1-(3-(4-fluorophenyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (40 mg, 0.083 mmol, 83%) as a yellow solid. MS ESI calcd. for C21H19FN5O [M+H]+ 376, found 376. 1H NMR (600 MHz, DMSO-d6) δ 13.24 (s, 1H), 9.12 (s, 1H), 9.06 (s, 1H), 8.04 (dd, J=8.8, 5.5 Hz, 2H), 7.75 (s, 1H), 7.65 (s, 1H), 7.39-7.27 (m, 6H), 7.22-7.18 (m, 1H), 4.86 (m, 1H), 1.39 (d, J=6.9 Hz, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified on reversed phase HPLC

Sources & evidence

ORD record
ord-f9a883d7b73d4fa6bbbcf058d0705051
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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