Trifluoroacetic acid → HCID 92044552, compound

HRID 571400Notes

Reaction equation

HRID 571400 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[C:11]3[CH:12]=[N:13][C:14]([NH:16][C:17]([NH:19][C@@H:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH3:21])=[O:18])=[CH:15][C:10]=3[N:9](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:8]=2)=[N:3]1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[C:11]3[CH:12]=[N:13][C:14]([NH:16][C:17]([NH:19][C@@H:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH3:21])=[O:18])=[CH:15][C:10]=3[NH:9][N:8]=2)=[N:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 89525834HCID 89525834, compound

Product 1

HCID 92044552HCID 92044552, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude (R)-1-(3-(1-methyl-1H-pyrazol-3-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (36 mg, 0.060 mmol) in DCM (1 mL) was treated with TFA (0.2 mL) and triethylsilane (0.02 mL, 0.125 mmol). The mixture was stirred at room temperature for 5.5 h, evaporated in vacuo and purified on reversed phase HPLC to afford (R)-1-(3-(1-methyl-1H-pyrazol-3-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (15.7 mg, 0.033 mmol, 55%) as a white solid. MS ESI calcd. For C19H20N7O [M+H]+ 362, found 362. 1H NMR (600 MHz, DMSO-d6) δ 13.06 (s, 1H), 9.16 (s, 1H), 9.12 (s, 1H), 7.84-7.79 (m, 1H), 7.78 (d, J=2.2 Hz, 1H), 7.57 (s, 1H), 7.35-7.27 (m, 4H), 7.21 (ddd, J=8.7, 5.8, 2.6 Hz, 1H), 6.68 (d, J=2.2 Hz, 1H), 4.97-4.71 (m, 1H), 3.93 (s, 3H), 1.39 (d, J=7.0 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-e7b8ef858bf044f08f18efaf9926bb30
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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