1,4-Dioxane hydrochloride → 1-(6-(1,4-Diazepan-1-yl)pyrazin-2-yl)-6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57891Notes

Reaction equation

HRID 57891 reaction equation
[F:1][C:2]([F:39])([F:38])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][N:17]([C:18]4[N:23]=[C:22]([N:24]5[CH2:30][CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]5)[CH:21]=[N:20][CH:19]=4)[C:11]=3[CH:10]=2)[CH:6]=[N:5]1.Cl.O1CCOCC1>O1CCOCC1>[N:24]1([C:22]2[N:23]=[C:18]([N:17]3[C:11]4[CH:10]=[C:9]([C:7]5[CH:6]=[N:5][N:4]([CH2:3][C:2]([F:39])([F:38])[F:1])[CH:8]=5)[N:14]=[CH:13][C:12]=4[CH:15]=[N:16]3)[CH:19]=[N:20][CH:21]=2)[CH2:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86707083tert-butyl 4-(6-(6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 727156181-(6-(1,4-Diazepan-1-yl)pyrazin-2-yl)-6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridineYield 84.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(6-(6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl)-1,4-diazepane-1-carboxylate (80 mg, 0.147 mmol) in 1,4-dioxane (6 mL) was added a solution of HCl/1,4-dioxane (3.8 M, 6 mL). The reaction mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure to give a crude product. The crude was purified by reverse phase preparative HPLC to afford 178 as a white solid (55 mg, 84%). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.17 (s, 1H), 8.60 (s, 1H), 8.54 (s, 1H), 8.37 (d, J=6.0 Hz, 2H), 8.09 (s, 1H), 8.02 (s, 1H), 5.26 (Q, J=9.2 Hz, 2H), 3.86 (s, 2H), 3.81 (s, 2H), 3.01 (t, J=5.5 Hz, 2H), 2.76 (t, J=5.5 Hz, 2H), 1.89 (t, J=5.5 Hz, 2H). MS (ESI) m/z: 444 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a crude product
  3. customThe crude was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-7a1e035223fe43888acca3c854d95bf7
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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