Stannous chloride dihydrate → HCID 67252536, compound

HRID 2042106Notes

Reaction equation

HRID 2042106 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[N:11]([O-])=O.[Na+].O.O.Cl[Sn]Cl.[CH3:20][CH:21]([CH3:27])[C:22](=O)[CH2:23][C:24]#[N:25]>Cl.C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:24]([NH2:25])=[CH:23][C:22]([CH:21]([CH3:27])[CH3:20])=[N:11]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

7

Reactant 4

HCID 61436Stannous chloride dihydrateHCID 880121H-Indazol-5-amineHCID 101299214-Methyl-3-oxopentanenitrileHCID 23668193Sodium Nitrite

Product 1

HCID 67252536HCID 67252536, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent

Procedure

To a solution of 1H-indazol-5-ylamine (8.0 g, 60.1 mmol) in concentrated HCl (20 mL, 240 mmol) was added an aqueous solution (50 mL) of NaNO2 (4.2 g, 60.1 mmol) at 0° C. and the resulting mixture was stirred for 1 h. A solution of SnCl2.2H2O (27 g, 120 mmol) in conc HCl (30 mL) was then added at 0° C. The reaction was stirred for an additional 2 h at RT. A solution of 4-methyl-3-oxo-pentanenitrile (8.0 g, 1.1 eq) in ethanol (50 mL) was added and the resultant mixture was heated to reflux overnight. The reaction mixture was concentrated under reduced pressure and was purified by silica gel chromatography to provide 2-(1H-indazol-5-yl)-5-isopropyl-2H-pyrazol-3-ylamine (8.5 g, 59% yield, two steps). 1H NMR (300 MHz, DMSO-d6) 8.09 (s, 1H), 7.82 (s, 1H), 7.57 (d, J=6.6 Hz, 1H), 7.51 (d, J=6.6 Hz, 1H), 5.31 (s, 1H), 5.12 (s, 2H), 2.74 (m, 1H), 1.15 (d, J=5.1 Hz, 6H); MS (ESI) m/z: 242.3 (M+H+).

Workup

  1. stirringThe reaction was stirred for an additional 2 h at RT
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-756a0b8ed2a04e2287d2a1e16562139c
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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