1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 57463869, compound

HRID 861158Notes

Reaction equation

HRID 861158 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[C:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[C:13]([C:14](=[O:16])[CH3:15])=[C:9]3[CH:8]=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.C(O[CH:30](OC(C)(C)C)[N:31]([CH3:33])[CH3:32])(C)(C)C>O>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[C:12]([C:17]4[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=4)[C:13]([C:14](=[O:16])/[CH:15]=[CH:30]/[N:31]([CH3:33])[CH3:32])=[C:9]3[CH:8]=[CH:7][CH:6]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 57494745HCID 57494745, compound

Product 1

HCID 57463869HCID 57463869, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-[7-(cyclopropylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]ethanone (1.22 g, 3.8 mmol) in N,N-dimethylformamide di-tert-butyl acetal (8 mL, 33 mmol) was heated under reflux for 4 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organics were washed with water and brine, then dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (1:1 hexanes-ethyl acetate to ethyl acetate) provided (2E)-1-[7-(cyclopropylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one (1.19 g, 83%) as a gold foam. 1H NMR (CDCl3): δ 7.73 (d, 1 H), 7.62 (d, 2 H), 7.34 (t, 1 H), 6.97 (d, 2 H), 6.37 (d, 1 H), 6.29 (s, 1 H), 5.13 (d, 1 H), 3.85 (s, 3 H), 2.95 (broad, 3 H), 2.65 (m, 1 H), 2.50 (broad, 3 H), 0.86 (m, 2 H), 0.72 (m, 2 H); MS m/z 377 (M+1).

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-1c4569c6e4fc41adbc64951d28c5a791
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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