Water → N-(cyclopropylmethyl)-N-ethylpyrazolo[1,5-a]pyridin-3-amine

HRID 859136Notes

Reaction equation

HRID 859136 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:9]([C:15]1[CH:16]=[N:17][N:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=12)[C:10]([CH:12]1[CH2:14][CH2:13]1)=O)[CH3:8].O.[OH-].[Na+]>C1COCC1>[CH:12]1([CH2:10][N:9]([CH2:7][CH3:8])[C:15]2[CH:16]=[N:17][N:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=23)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69588311N-ethyl-N-pyrazolo[1,5-a]pyridin-3-ylcyclopropanecarboxamide

Product 1

HCID 69588967N-(cyclopropylmethyl)-N-ethylpyrazolo[1,5-a]pyridin-3-amineYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (0.70 g, 18.5 mmol) in THF (2.0 mL) was added a solution of N-ethyl-N-pyrazolo[1,5-a]pyridin-3-ylcyclopropanecarboxamide (0.77 g, 3.36 mmol) in THF (5.0 mL) at room temperature and stirred for 16 h. H2O (0.70 mL), 15% NaOH (0.70 mL) and H2O (2.1 mL) were added sequentially. Celite was added and filtered. The filtrate was concentrated in vacuo to dryness and the residue was subjected to column chromatography (E:H=1:4) to give 0.30 g (42%) of yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=7.0 Hz, 1H), 7.82 (s, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.02–6.98 (m, 1H), 6.70–6.66 (m, 1H), 3.21 (q, J=7.1 Hz, 2H), 2.92 (d, J=6.6 Hz, 2H), 1.06 (t, J=7.1 Hz, 3H), 0.92–0.88 (m, 1H), 0.46–0.41 (m, 2H), 0.11–0.08 (m, 2H); MS (EI) m/z 216.19 (M++H).

Workup

  1. additionCelite was added
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-704d16b44b65481188786dde73cd8f91
Source dataset
uspto-grants-2006_12
Patent number
US07151109B2

Reaction notes

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