1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 69449611, compound

HRID 1296703

Reaction equation

HRID 1296703 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[C:15]([C:16](=[O:18])[CH3:17])=[C:11]3[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[CH:31](OC(C)(C)C)[N:32]([CH3:34])[CH3:33])(C)(C)C>>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:19]4[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=4)[C:15]([C:16](=[O:18])[CH:17]=[CH:31][N:32]([CH3:34])[CH3:33])=[C:11]3[CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 694487401-[7-(Cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]ethanone

Product 1

HCID 69449611HCID 69449611, compoundYield 69%

Conditions

Temperature
80 °C

Procedure

To 1-[7-(cyclopentylamino)-2-(4fluorophenyl)pyrazolo[1,5- c]pyrimidin-3-yl]ethanone (200 mg, 0.59 mmol) was added 1,1 -di-tert-butoxy-N,N-dimethylmethanamine (4 mL) and the mixture heated to 80° C. for 30 minutes. The reaction was let cool to room temperature and was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic layers washed with water and brine. The ethyl acetate solution was dried over magnesium sulfate, filtered and concentrated. The resulting residue was purified by silica chromatography eluting with ethyl acetate to yield 160 mg (69%) of 1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]-3-(dimethylamino)prop-2-en-1-one. 1H NMR (CDCl3): δ 7.77 (m, 4H), 7.44 (d, 1H), 7.19 (t, 2H), 6.41 (d, 1H), 5.09 (d, 1H), 4.57 (m,1H), 3.07 (m, 3H), 2.60 (m, 3H), 2.25 (m, 2H), 1.85 (m, 6H). MS m/z 394 (M+1).

Workup

  1. temperatureThe reaction was let cool to room temperature
  2. customwas partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers washed with water and brine
  5. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-73c873095ea74f5883eafeaee0dadd4c
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Linked notes

Loading…