Water → 5-((2Z)-2-((1-(difluoroboryl)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2H-pyrrol-5-yl)-N-(2-((3,5-difluoro-4-(trimethylsilyl)phenyl)amino)-1-(4-(methoxymethyl)phenyl)-2-oxoethyl)pentanamide

HRID 2202335노트

반응식

HRID 2202335 반응식
[NH2:1][CH:2]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][O:25][CH3:26])=[CH:20][CH:19]=1)[C:3]([NH:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[C:8]([F:17])[CH:7]=1)=[O:4].[F:27][B:28]([F:56])[N:29]1[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[C:30]1/[CH:36]=[C:37]1\[N:38]=[C:39]([CH2:42][CH2:43][CH2:44][CH2:45][C:46](ON2C(=O)CCC2=O)=[O:47])[CH:40]=[CH:41]\1.O.O.C(#N)C>CN(C=O)C>[F:56][B:28]([F:27])[N:29]1[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[C:30]1/[CH:36]=[C:37]1\[N:38]=[C:39]([CH2:42][CH2:43][CH2:44][CH2:45][C:46]([NH:1][CH:2]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][O:25][CH3:26])=[CH:22][CH:23]=2)[C:3]([NH:5][C:6]2[CH:11]=[C:10]([F:12])[C:9]([Si:13]([CH3:14])([CH3:15])[CH3:16])=[C:8]([F:17])[CH:7]=2)=[O:4])=[O:47])[CH:40]=[CH:41]\1

참가 물질

6

반응물 4

HCID 962WaterHCID 103646301-((5-((2Z)-2-((1-(difluoroboryl)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2H-pyrrol-5-yl)pentanoyl)oxy)pyrrolidine-2,5-dioneHCID 18373917Acetonitrile--water (1/1)HCID 1317357652-amino-N-(3,5-difluoro-4-(trimethylsilyl)phenyl)-2-(4-(methoxymethyl)phenyl) acetamide

생성물 1

HCID 1317357665-((2Z)-2-((1-(difluoroboryl)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2H-pyrrol-5-yl)-N-(2-((3,5-difluoro-4-(trimethylsilyl)phenyl)amino)-1-(4-(methoxymethyl)phenyl)-2-oxoethyl)pentanamide수율 55.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the crude 2-amino-N-(3,5-difluoro-4-(trimethylsilyl)phenyl)-2-(4-(methoxymethyl)phenyl)acetamide (9.07 mg, 0.02 mmol) in DMF (0.5 mL) was added 1-((5-((2Z)-2-((1-(difluoroboryl)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2H-pyrrol-5-yl)pentanoyl)oxy)pyrrolidine-2,5-dione (BODIPY (registered trademark) FL-C5 succinimidyl ester) (5.0 mg, 0.01 mmol) at room temperature, and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; ethyl acetate/hexane), and then preparative HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% TFA)) to give 5-((2Z)-2-((1-(difluoroboryl)-3,5-dimethyl-1H-pyrrol-2-yl)methylene)-2H-pyrrol-5-yl)-N-(2-((3,5-difluoro-4-(trimethylsilyl)phenyl)amino)-1-(4-(methoxymethyl)phenyl)-2-oxoethyl)pentanamide (3.8 mg, 5.58 μmol, 46.6%) as an orange solid, which is a fluorescent-labeled synthetic ligand.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent; ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-241b26c5805c4fc692e8b5a386553aa5
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365520B2

반응 노트

불러오는 중…