Acetic Acid → HCID 89852127, compound

HRID 1746897Notes

Reaction equation

HRID 1746897 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][N:5]([C:8]2[N:18]=[CH:17][CH:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=1)=O.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(O)(=O)C>C(#N)C>[O:22]1[CH2:23][CH2:24][N:19]([CH2:1][C:3]2[CH:7]=[CH:6][N:5]([C:8]3[N:18]=[CH:17][CH:16]=[CH:15][C:9]=3[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8083MorpholineHCID 89851914HCID 89851914, compound

Product 1

HCID 89852127HCID 89852127, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 2-(3-formyl-1H-pyrazol-1-yl)nicotinate (400 mg, 1.631 mmol) and morpholine (220 μl, 2.53 mmol) in acetonitrile (25 mL) NaCNBH4 (130 mg, 2.069 mmol) was added, and the pH adjusted to 5-6 by adding glacial acetic acid (110 μL, 1.922 mmol). The mixture was stirred at room temperature for 1 h, another portion of NaCNBH4 (30 mg, 0.477 mmol) added and stirred for 2 hrs. For work up the mixture was concentrated, dissolved in 100 mL of dichloromethane, washed subsequently with water and brine, dried (MgSO4), filtered off and concentrated to give 710 mg of the crude title product. Purification by chromatography over silica gel (CH2Cl2/3%-5% methanol) and concentration yielded 518 mg of the title compound as clear oil; ESI-MS [M+H]+: 317.20.

Workup

  1. additionanother portion of NaCNBH4 (30 mg, 0.477 mmol) added
  2. stirringstirred for 2 hrs
  3. concentrationFor work up the mixture was concentrated
  4. dissolutiondissolved in 100 mL of dichloromethane
  5. washwashed subsequently with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered off
  8. concentrationconcentrated
  9. customto give 710 mg of the crude title product
  10. customPurification by chromatography
  11. concentrationover silica gel (CH2Cl2/3%-5% methanol) and concentration

Sources & evidence

ORD record
ord-9121e433d39242f086bc453f126dbdb4
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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