Ammonium Chloride → HCID 72714859, compound

HRID 57993Notes

Reaction equation

HRID 57993 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[CH:11][C:10]3[CH:13]=[N:14][N:15]([C:16]4[N:21]=[C:20]([N:22]5[CH2:25][C:24]([CH2:27][N+:28]([O-])=O)([OH:26])[CH2:23]5)[CH:19]=[CH:18][CH:17]=4)[C:9]=3[CH:8]=2)[CH:4]=[N:3]1.[NH4+].[Cl-]>CO.O.[Zn]>[NH2:28][CH2:27][C:24]1([OH:26])[CH2:23][N:22]([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([N:15]3[C:9]4[CH:8]=[C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)[N:12]=[CH:11][C:10]=4[CH:13]=[N:14]3)[N:21]=2)[CH2:25]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 867071771-(6-(6-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-3-(nitromethyl)azetidin-3-ol

Product 1

HCID 72714859HCID 72714859, compoundYield 64.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-3-(nitromethyl)azetidin-3-ol (100 mg, 0.25 mmol) in MeOH (5 mL) and H2O (0.5 mL) was added Zn powder (129 mg, 2 mmol) and NH4Cl (132 mg, 2.5 mmol). The reaction mixture was stirred at ambient temperature for 2 hours and filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC to afford 270 as red solid (60 mg, 64.8%). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.13 (s, 1H), 8.75 (s, 1H), 8.53 (s, 1H), 8.34-8.40 (m, 2H), 7.98 (s, 1H), 7.72-7.75 (m, 1H), 7.24-7.25 (m, 1H), 6.34-6.36 (d, J=8.5 Hz, 1H), 4.23-4.25 (d, J=8.5 Hz, 2H), 3.89-3.97 (m, 5H), 3.06-3.10 (m, 2H); MS (ESI) m/z: 377 [M+H]+.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-88c5614a5131440aadd7d60d28c9fb3d
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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