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18-Crown-6 → HCID 178435251, 화합물

HRID 1594901
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HRID 1594901 반응식
C(OC([N:8]1[C:12]2[CH:13](C3C=CC(C#N)=C(F)C=3)[N:14]([C:17](OC(C)(C)C)=O)[CH2:15][CH2:16][C:11]=2[N:10]=[CH:9]1)=O)(C)(C)C.[CH2:33]([C:35]1([C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([OH:50])[CH:45]=2)[CH2:41][CH2:40][CH2:39][CH2:38][N:37]([CH3:42])[C:36]1=[O:43])[CH3:34].[F-].[K+].C1O[CH2:69][CH2:68]OCCOCCOCCOCCOC1>CC#N>[CH2:33]([C:35]1([C:44]2[CH:45]=[C:46]([CH:47]=[CH:48][CH:49]=2)[O:50][C:69]2[CH:68]=[C:17]([N:14]3[C:13]4[NH:10][CH:9]=[N:8][C:12]=4[CH2:11][CH2:16][CH2:15]3)[CH:15]=[CH:16][C:11]=2[C:12]#[N:8])[CH2:41][CH2:40][CH2:39][CH2:38][N:37]([CH3:42])[C:36]1=[O:43])[CH3:34]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 27945733-Ethylhexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-oneHCID 540442074-(4-Cyano-3-fluoro-phenyl)-6,7-dihydro-4h-imidazo [4,5-c]pyridine-3,5-dicarboxylic acid di-tert-butyl ester

생성물 1

HCID 178435251HCID 178435251, 화합물

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

4-(4-Cyano-3-fluoro-phenyl)-6,7-dihydro-4H-imidazo[4,5-c]pyridine-3,5-dicarboxylic acid di-tert-butyl ester (as described above in Step B) (0.120 g, 0.270 mmol), 3-ethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one (0.067 g, 0.270 mmol), KF.Al2O3 (0.080 g) and 18-Crown-6 (0.007 g) were refluxed in CH3CN (5 mL) under Ar for 24 h. The solution was filtered and concentrated in vacuo. The residue was dissolved in CH2Cl2 (10 mL) and TFA (5 mL) and stirred at RT for ½ h. The solution was concentrated in vacuo, purified using reverse phase chromatography (95/5 to 5/95 H2O/CH3CN w/0.1% TFA, flow=65 mL/min), lyophilized, and then further separated into two diastereomers using a Chiralpak AS column.

후처리

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (10 mL)
  4. concentrationThe solution was concentrated in vacuo
  5. custompurified
  6. customfurther separated into two diastereomers

출처 및 근거

ORD 기록
ord-64933a4464a84314a4561094285028fd
출처 데이터셋
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06284755B1

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