Ethyl acetate hexane → HCID 69588808, compound

HRID 859139Notes

Reaction equation

HRID 859139 reaction equation
[CH2:1]([C:3]1[C:11]([N:12]([CH2:18][CH2:19][CH2:20][F:21])[C:13](=O)[CH2:14][O:15][CH3:16])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].C(OCC)(=O)C.CCCCCC>C1COCC1>[CH2:1]([C:3]1[C:11]([N:12]([CH2:18][CH2:19][CH2:20][F:21])[CH2:13][CH2:14][O:15][CH3:16])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 69588397HCID 69588397, compound

Product 1

HCID 69588808HCID 69588808, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-(3-fluoropropyl)-2-methoxyacetamide (1.62 g, 5.5 mmol) in THF (25 mL) was treated with borane dimethyl sulfide complex (1.1 mL, 11.0 mmol). The reaction was stirred at room temperature for 5.5 hours. The reaction was quenched with 2N HCl then made basic with 4N NaOH. The mixture was extracted twice with ethyl acetate. The combined organic layers was washed with brine, dried over MgSO4 and concentrated in vacuo to give a yellow oil which was subjected to column chromatography (40% ethyl acetate/hexane) to give 0.313 g (20%) of yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 8.99 (d, J=7.2 Hz, 1H), 7.68 (d, J=8.8 Hz, 1H), 7.41–7.37 (m, 1H), 7.10–7.07 (m, 1H), 4.62 (dt, J=47.2, 5.7 Hz, 2H), 3.39–3.29 (m, 9H), 3.05 (q, J=7.5 Hz, 2H), 1.86–1.73 (m, 2H), 1.35 (t, J=7.5 Hz, 3H); MS (EI) m/z 280.24 (M++H).

Workup

  1. customThe reaction was quenched with 2N HCl
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. washThe combined organic layers was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil which

Sources & evidence

ORD record
ord-62b808c58b97424a9cb9522dd06893bb
Source dataset
uspto-grants-2006_12
Patent number
US07151109B2

Reaction notes

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