Ethyl acetate hexane → HCID 45095432, compound

HRID 859140Notes

Reaction equation

HRID 859140 reaction equation
[CH2:1]([C:3]1[C:11]([N:12]([CH2:18][CH2:19][CH2:20][F:21])C(=O)COC)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.CCCCCC>C1COCC1>[CH2:1]([C:3]1[C:11]([NH:12][CH2:18][CH2:19][CH2:20][F:21])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydrideHCID 69588397HCID 69588397, compound

Product 1

HCID 45095432HCID 45095432, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-(2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-(3-fluoropropyl)-2-methoxyacetamide (1.00 g, 3.39 mmol) in THF (12 mL) was added to a slurry of LAH (1.05 g, 27.7 mmol) in THF (6 mL) and the reaction was stirred at room temperature for 3.25 hours. The reaction was cooled to 0° C. and quenched with water (1 mL), 15% NaOH (3 mL) and water (3 mL). The mixture was filtered through diatomaceous earth and the filtrate was extracted with CH2Cl2, dried over MgSO4 and concentrated in vacuo to give a brown oil which was subjected to column chromatography (50% ethyl acetate/hexane) to give 0.568 g (75%) of yellow oil as the title compound: 1H NMR (400 MHz, DMSO-d6) δ 8.38 (d, J=7.0 Hz, 1H), 7.49 (d, J=9.0 Hz, 1H), 6.98–6.94 (m, 1H), 6.63–6.60 (m, 1H), 4.52 (dt, J=47.5, 5.9 Hz, 2H), 4.10 (br, 1H), 3.04 (t, J=6.9 Hz, 2H), 2.70 (q, J=7.6 Hz, 2H), 1.89–1.76 (m, 2H), 1.24 (t, J=7.6 Hz, 3H); 13C NMR (100 MHz, DMSO-d6) δ 148.8, 133.1, 128.1, 120.7, 118.5, 116.0, 110.1, 81.1 (d, J=160.6 Hz), 45.6 (d, J=5.2 Hz), 30.8 (d, J=19.2 Hz), 18.6, 13.4; 19F NMR (376 MHz, DMSO-d6) −219.0 (m); HRMS (FAB) calcd for C12H16FN3+H 222.1406. found 222.1403.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with water (1 mL), 15% NaOH (3 mL) and water (3 mL)
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. extractionthe filtrate was extracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil which

Sources & evidence

ORD record
ord-d0438730906c4ee99c062177456de35a
Source dataset
uspto-grants-2006_12
Patent number
US07151109B2

Reaction notes

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