Hydrazine hydrate (1:1) → 1-[(2-fluoro-3-pyridinyl)methyl]-1H-pyrazol-3-amine

HRID 1625077Notes

Reaction equation

HRID 1625077 reaction equation
[F:1][C:2]1[C:7]([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([N:14]3C(=O)C4C(=CC=CC=4)C3=O)=[N:10]2)=[CH:6][CH:5]=[CH:4][N:3]=1.O.NN>C(O)C>[F:1][C:2]1[C:7]([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([NH2:14])=[N:10]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 682779802-{1-[(2-fluoro-3-pyridinyl)methyl]-1H-pyrazol-3-yl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 866916131-[(2-fluoro-3-pyridinyl)methyl]-1H-pyrazol-3-amineYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Intermediate 46 (180 mg, 0.558 mmol) and hydrazine monohydrate (FLUKA, 0.035 mL, 1.117 mmol) in ethanol (10 mL) was stirred at room temperature for 4 h. Precipitate was filtered and washed with DCM. Filtrate was evaporated to dryness. Residue was purified by silica column chromatography using a linear gradient of DCM/MeOH as eluents to yield the title compound (102 mg, 0.53 mmol, 95% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm: 8.15 (m, 1H), 7.57-7.62 (m, 1H), 7.45 (d, 1H), 7.29-7.33 (m, 1H), 5.41 (d, 1H), 5.08 (s, 2H), 4.62 (br s, 2H). [ES+MS] m/z 193 (MH+).

Workup

  1. filtrationPrecipitate was filtered
  2. washwashed with DCM
  3. customFiltrate was evaporated to dryness
  4. customResidue was purified by silica column chromatography

Sources & evidence

ORD record
ord-7c4d59a638a34a80980bfea811496ac5
Source dataset
uspto-grants-2014_07
Patent number
US08779153B2

Reaction notes

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