Hydrochloric Acid → Lp-PLA2-IN-1

HRID 920364

반응식

HRID 920364 반응식
Cl[C:2]1[CH:12]=[C:6]2[N:7]([CH3:11])[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=1.[F:14][C:15]1[CH:16]=[C:17]([CH2:33][OH:34])[CH:18]=[C:19]([F:32])[C:20]=1[O:21][C:22]1[CH:23]=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=1.[H-].[Na+].Cl>CN(C)C=O>[F:14][C:15]1[CH:16]=[C:17]([CH:18]=[C:19]([F:32])[C:20]=1[O:21][C:22]1[CH:23]=[N:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=1)[CH2:33][O:34][C:2]1[CH:12]=[C:6]2[N:7]([CH3:11])[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 66825487(3,5-Difluoro-4-((6-(trifluoromethyl)-3-pyridinyl)oxy)phenyl)methanol2회HCID 717434718-Chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-one

생성물 1

HCID 71236597Lp-PLA2-IN-1수율 28%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The title compound was prepared by a procedure similar to that described for E1 starting from 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one and (3,5-difluoro-4-((6-(trifluoromethyl)pyridin-3-yl)oxy)phenyl)methanol. An exemplary process is shown below: To a solution of 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-c]pyrimidin-6(2H)-one, trifluoroacetic acid salt (43 mg, 0.137 mmol) and (3,5-difluoro-4-((6-(trifluoromethyl)pyridin-3-yl)oxy)phenyl)methanol (46.0 mg, 0.151 mmol) in N,N-dimethylformamide (DMF) (1.5 mL) were added NaH (16.45 mg, 0.411 mmol). The mixture was stirred at room temperature for 30 mins. Sufficient aqueous HCl solution (1 M) was added to adjust the solution to pH to ˜7. The resulted mixture was purified by Mass Directed AutoPrep (basic mobile phase) to afford the title compound (18 mg, 0.038 mmol, 28.0% yield) as a white solid.

후처리

  1. customThe title compound was prepared by a procedure similar to
  2. customThe resulted mixture was purified by Mass Directed AutoPrep (basic mobile phase)

출처 및 근거

ORD 기록
ord-5d31e3912ec14110b258e1b5f2f2e1d0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273054B2

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