tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate → 1-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57867Notes

Reaction equation

HRID 57867 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:9]=[C:8]([C:10]3[N:15]=[CH:14][C:13]4[CH:16]=[N:17][N:18]([C:19]5[N:24]=[C:23]([N:25]6[CH2:31][CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]6)[CH:22]=[CH:21][CH:20]=5)[C:12]=4[CH:11]=3)[CH:7]=[N:6]2)[CH2:3][CH2:2]1>Cl.CO>[N:25]1([C:23]2[N:24]=[C:19]([N:18]3[C:12]4[CH:11]=[C:10]([C:8]5[CH:7]=[N:6][N:5]([CH2:4][CH:1]6[CH2:3][CH2:2]6)[CH:9]=5)[N:15]=[CH:14][C:13]=4[CH:16]=[N:17]3)[CH:20]=[CH:21][CH:22]=2)[CH2:31][CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1

Participants

3

Reactant 1

HCID 86707060tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 867070631-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridineYield 43.5%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A solution of tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]-pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (200 mg, 0.39 mmol) in HCl/MeOH (2M, 10 mL) was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. The crude was purified by reverse phase preparative HPLC to afford 161 as a yellow solid (70 mg, 43.5%). 1H NMR (500 MHz, CDCl3) δ (ppm) 9.055-9.057 (d, J=1 Hz, 1H), 8.74 (s, 1H), 8.23 (s, 1H), 8.17 (s, 1H), 7.97 (s, 1H), 7.60-7.63 (t, J=16 Hz, 1H), 7.28 (s, 1H), 6.41-6.43 (d, J=8 Hz, 1H), 4.04-4.06 (d, J=7 Hz, 2H), 3.89-3.94 (m, 4H), 3.17-3.19 (t, J=11 Hz, 2H), 2.91-2.93 (t, J=11.5 Hz, 2H), 2.03-2.06 (t, J=12.5 Hz, 2H), 1.35-1.36 (m, 1H), 0.69-0.73 (m, 2H), 0.43-0.46 (m, 2H); MS (ESI) m/z: 415 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe crude was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-b7f7a9aa35ad4884adf91250e9fae0fc
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

Loading…