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

HRID 57848Notes

Reaction equation

HRID 57848 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([C:10]2[N:15]=[CH:14][C:13]3[CH:16]=[N:17][N:18]([C:19]4[N:24]=[C:23]([N:25]5[CH2:31][CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]5)[CH:22]=[CH:21][CH:20]=4)[C:12]=3[CH:11]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.N>C(Cl)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]([C:1]([CH3:4])([CH3:3])[CH3:2])[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

6

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 86707048tert-butyl 4-(6-(6-(1-tert-butyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 727153781-(6-(1,4-Diazepan-1-yl)pyridin-2-yl)-6-(1-tert-butyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridineYield 56.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(6-(6-(1-tert-butyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (100 mg, 0.19 mmol) and TFA (2 mL) in DCM (4 mL) was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure to afford a residue. The residue was diluted with MeOH (10 mL), neutralized with 28% ammonia solution, concentrated, and purified by preparative HPLC to afford 145 as a white solid (45 mg, 56%). 1H-NMR (500 MHz, CD3OD) δ (ppm) 9.03 (s, 1H), 8.71 (d, J=6.5 Hz, 1H), 8.36 (s, 1H), 8.28 (s, 1H), 7.98 (s, 1H), 7.65-7.68 (m, 1H), 7.25 (d, J=7.5 Hz, 1H), 6.58 (d, J=8.5 Hz, 1H), 3.90-3.94 (m, 4H), 3.14-3.16 (m, 2H), 2.91-2.94 (m, 2H), 2.05-2.10 (m, 2H), 1.68 (s, 9H); MS (ESI) m/z: 417 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford a residue
  3. concentrationconcentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-a9f4970851e54ea6b2f5174113a6d3ff
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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