Acetic Acid → 5-Fluoro-6-[(tetrahydro-4H-pyran-3-yl)propylamino]benzoxazolin-2-one

HRID 1533875노트

반응식

HRID 1533875 반응식
[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[O:13]1[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][CH2:20][CH:21]=O)[CH2:14]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[F:12][C:11]1[C:2]([NH:1][CH2:21][CH2:20][CH2:19][CH:15]2[CH2:16][CH2:17][CH2:18][O:13][CH2:14]2)=[CH:3][C:4]2[O:8][C:7](=[O:9])[NH:6][C:5]=2[CH:10]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 156759596-Amino-5-fluoro-2,3-dihydro-1,3-benzoxazol-2-oneHCID 15676001Tetrahydro-2H-pyran-3-propanal

생성물 1

HCID 678348985-Fluoro-6-[(tetrahydro-4H-pyran-3-yl)propylamino]benzoxazolin-2-one수율 38.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 6-amino-5-fluoro-benzoxazolin-2-one (2.1 g, 12.5 mmole) in methanol (80 ml) were added 3-(tetrahydro-2H-pyran-3-yl) propanal (1.95 g, 13.7 mmole) and acetic acid (1 ml) at room temperature, and then the mixture was stirred for 1 hour. Sodium cyanoborohydride (0.867 g, 13.7 mmole) was combined and stirring continued for 17 hours at room temperature. The reaction mixture was concentrated in vacuo, and the residue was treated with aqueous ammonium chloride solution. The organic substance was extracted with ethyl acetate/tetrahydrofuran. The extracts were washed with brine, dried over magnesium sulfate, and concentrated to afford crude product. This crude product was recrystallized from methanol to give 1.40 g of the title compound: m.p. 144°-145° C.

후처리

  1. stirringstirring
  2. waitcontinued for 17 hours at room temperature
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionthe residue was treated with aqueous ammonium chloride solution
  5. extractionThe organic substance was extracted with ethyl acetate/tetrahydrofuran
  6. washThe extracts were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto afford crude product
  10. customThis crude product was recrystallized from methanol

출처 및 근거

ORD 기록
ord-70c0d0afe04049e9bd90abb0d2b8e60c
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05086062

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