Water → HCID 22346421, 화합물

HRID 897343노트

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HRID 897343 반응식
[C:1]([N:4]1[CH:8]([C:9]2[N:18]=[C:17]([C:19]([O:21]C)=O)[C:16]([O:23]CC3C=CC(OC)=CC=3)=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[N:14]3)[CH2:7][CH2:6][N:5]1[CH3:33])(=[O:3])[CH3:2].O.[C:35](O)([C:37]([F:40])(F)F)=O>C(#N)C>[C:1]([N:4]1[CH:8]([C:9]2[N:18]=[C:17]([C:19]([NH:14][CH2:15][C:10]3[CH:11]=[CH:35][C:37]([F:40])=[CH:8][CH:9]=3)=[O:21])[C:16]([OH:23])=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[N:14]3)[CH2:7][CH2:6][N:5]1[CH3:33])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 22346322HCID 22346322, 화합물

생성물 1

HCID 22346421HCID 22346421, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

A solution of the above acetylpyrazolidine (50 mg, Step 1), water (0.25 mL), and TFA (0.15 mL) in acetonitrile (5 mL) was stirred at room temperature for 6 hours. The resultant mixture was concentrated under vacuum. Residual water and TFA was removed by co-evaporation with additional acetonitrile (3×5 mL). Without further purification, the residual oil was treated with 4-fluorobenzylamine (0.2 mL) in a mixture of methanol (1 mL) and toluene (8 mL) in a sealed tube was heated in an oil bath at 120° C. for 2 hours. The product mixture was concentrated under vacuum. The residue was dissolved in DMSO, and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound.

후처리

  1. concentrationThe resultant mixture was concentrated under vacuum
  2. customResidual water and TFA was removed by co-evaporation with additional acetonitrile (3×5 mL)
  3. customWithout further purification
  4. additionthe residual oil was treated with 4-fluorobenzylamine (0.2 mL) in a mixture of methanol (1 mL) and toluene (8 mL) in a sealed tube
  5. concentrationThe product mixture was concentrated under vacuum
  6. dissolutionThe residue was dissolved in DMSO
  7. customsubjected to HPLC purification on C-18 stationary phase
  8. washeluted with water/acetonitrile/TFA mobile phase
  9. customCollection and lyophilization of appropriate fractions

출처 및 근거

ORD 기록
ord-5061fef0435248c88cc827d80b927830
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921759B2

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