Hydrochloric Acid → 6-(1-(6-(1,4-diazepan-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)pyrazin-2-amine

HRID 57963Notes

Reaction equation

HRID 57963 reaction equation
COC1C=CC(C[NH:10][C:11]2[N:16]=[C:15]([C:17]3[N:22]=[CH:21][C:20]4[CH:23]=[N:24][N:25]([C:26]5[N:31]=[C:30]([N:32]6[CH2:38][CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]6)[CH:29]=[CH:28][CH:27]=5)[C:19]=4[CH:18]=3)[CH:14]=[N:13][CH:12]=2)=CC=1.Cl.OS(C(F)(F)F)(=O)=O>ClCCl.O1CCOCC1>[N:32]1([C:30]2[N:31]=[C:26]([N:25]3[C:19]4[CH:18]=[C:17]([C:15]5[N:16]=[C:11]([NH2:10])[CH:12]=[N:13][CH:14]=5)[N:22]=[CH:21][C:20]=4[CH:23]=[N:24]3)[CH:27]=[CH:28][CH:29]=2)[CH2:38][CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 62406Trifluoromethanesulfonic acidHCID 86707145Tert-butyl 4-[6-[6-[6-[(4-methoxyphenyl)methylamino]pyrazin-2-yl]pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-1,4-diazepane-1-carboxylate

Product 1

HCID 867071466-(1-(6-(1,4-diazepan-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)pyrazin-2-amineYield 27.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of tert-butyl 4-[6-[6-[6-[(4-methoxyphenyl)methylamino]pyrazin-2-yl]pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-1,4-diazepane-1-carboxylate (0.4789 mmol; 291 mg) in Dichloromethane (5 mL) was added Hydrogen Chloride, 4.0 M in 1,4-Dioxane (5 mL), and TRIFLIC ACID (4.789 mmol; 733.3 mg; 0.4293 mL). The reaction mixture was stirred at room temperature for 3 days. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 247 as an off-white solid (50.3 mg, 27%). 1H NMR (400 MHz, DMSO) δ 9.45-9.41 (s, 1H), 9.26-9.22 (s, 1H), 8.76-8.73 (s, 1H), 8.64-8.58 (s, 1H), 7.99-7.96 (s, 1H), 7.73-7.67 (t, J=8.1 Hz, 1H), 7.16-7.12 (d, J=7.7 Hz, 1H), 6.63-6.58 (d, J=8.5 Hz, 1H), 6.33-6.25 (s, 2H), 3.89-3.82 (dd, J=11.0, 5.2 Hz, 4H), 3.03-2.98 (m, 2H), 2.73-2.66 (m, 2H), 1.91-1.84 (dd, J=11.5, 5.8 Hz, 2H); MS (ESI) m/z: 388.2 [M+H]+

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8f3f90c2729345d1872da6667797476b
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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