Hydrochloric Acid → 3-amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one

HRID 2070177

반응식

HRID 2070177 반응식
[O:1]=[C:2]1[CH:11]([NH:12]C(=O)OC(C)(C)C)[CH2:10][C:9]2[C:4](=[C:5]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:26][C:27]1[CH:31]=[CH:30][S:29][CH:28]=1.Cl.C(=O)(O)[O-].[K+]>C(OCC)(=O)C.O>[NH2:12][CH:11]1[CH2:10][C:9]2[C:4](=[C:5]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:2]1=[O:1]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 516893Potassium BicarbonateHCID 59620385Tert-butyl 2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

생성물 1

HCID 596203303-amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
37.5 °C

실험 절차

tert-Butyl 2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (5.0 g) was suspended in ethyl acetate (30 mL), and 4N hydrochloric acid in ethyl acetate (28.3 mL) was added thereto, followed by stirring at 35-40° C. for one hour. The reaction mixture was added to a solution of potassium bicarbonate (11.3 g) in water (20 mL), and the mixture was partitioned at 45° C. The aqueous layer was extracted with ethyl acetate twice, and the organic layers were combined. The combined organic layer was concentrated under reduced pressure until precipitates were formed. The concentrated residue was stirred at room temperature for 30 minutes, and the formed precipitates were recovered through filtration. The thus-obtained solid was washed with ethyl acetate, and then dried under reduced pressure, whereby the title compound (2.93 g) was yielded as crystals.

후처리

  1. customthe mixture was partitioned at 45° C
  2. extractionThe aqueous layer was extracted with ethyl acetate twice
  3. concentrationThe combined organic layer was concentrated under reduced pressure
  4. customuntil precipitates
  5. customwere formed
  6. stirringThe concentrated residue was stirred at room temperature for 30 minutes
  7. customthe formed precipitates
  8. filtrationwere recovered through filtration
  9. washThe thus-obtained solid was washed with ethyl acetate
  10. dry with materialdried under reduced pressure, whereby the title compound (2.93 g)
  11. customwas yielded as crystals

출처 및 근거

ORD 기록
ord-70eed306f3944569ad49b34dab2c2ae0
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299255B2

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