Ethyl Acetate → HCID 67008667, compound

HRID 2062752Notes

Reaction equation

HRID 2062752 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][C:12]3[NH:16][N:15]=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.N12CCCN=C1CCCCC2.[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH:43]([C:48](=O)[CH2:49][CH2:50][CH2:51][CH3:52])[C:44](OC)=[O:45])=[CH:38][CH:37]=1)#[N:29].C(OCC)(=O)C>CCN(C1C=CC=CC=1)CC.O>[CH2:49]([C:48]1[N:16]2[N:15]=[CH:14][CH:13]=[C:12]2[N:11]([CH:8]2[CH2:7][CH2:6][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:10][CH2:9]2)[C:44](=[O:45])[C:43]=1[CH2:42][C:39]1[CH:38]=[CH:37][C:36]([C:31]2[C:30]([C:28]#[N:29])=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:41][CH:40]=1)[CH2:50][CH2:51][CH3:52]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10807723Methyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoateHCID 67009993N-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amine

Product 1

HCID 67008667HCID 67008667, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7061N,N-DiethylanilineSolvent

Procedure

A solution of N-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-5-amine (2.2 g), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.30 mL) and methyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoate (7.0 g) in diethylaniline (10 mL) was stirred at 180° C. for 2 hr. The mixture was allowed to cool, ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (3.6 g, 69%).

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3c3463c4c38b4f4c992058b491e2be31
Source dataset
uspto-grants-2012_10
Patent number
US08283353B2

Reaction notes

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