Water → Perfluorophenyl 4-(2-chloro-3'-fluoro-5-methoxy-[1,1'-biphenyl]-4-yl)quinazoline-7-sulfonate

HRID 1473684노트

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HRID 1473684 반응식
C([S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:19]3[C:24]([O:25][CH3:26])=[CH:23][C:22]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=4)=[C:21]([Cl:34])[CH:20]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.ClN1C(C)(C)C(=[O:43])N(Cl)C1=O.[F:46][C:47]1[C:52]([F:53])=[C:51]([F:54])[C:50]([F:55])=[C:49]([F:56])[C:48]=1[OH:57].C(N(CC)CC)C.[OH2:65]>C(O)(=O)C.C(Cl)Cl>[Cl:34][C:21]1[CH:20]=[C:19]([C:13]2[C:12]3[C:17](=[CH:18][C:9]([S:8]([O:57][C:48]4[C:47]([F:46])=[C:52]([F:53])[C:51]([F:54])=[C:50]([F:55])[C:49]=4[F:56])(=[O:43])=[O:65])=[CH:10][CH:11]=3)[N:16]=[CH:15][N:14]=2)[C:24]([O:25][CH3:26])=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1

참가 물질

8

반응물 5

HCID 962WaterHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 866877667-(Benzylthio)-4-(2-chloro-3'-fluoro-5-methoxy-[1,1'-biphenyl]-4-yl)quinazoline

생성물 1

HCID 86687767Perfluorophenyl 4-(2-chloro-3'-fluoro-5-methoxy-[1,1'-biphenyl]-4-yl)quinazoline-7-sulfonate

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매2회

실험 절차

A round-bottom flask was charged with 7-(benzylthio)-4-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)quinazoline (0.490 g, 1.006 mmol), DCM (9.47 ml), DCM (9.47 ml), Acetic Acid (0.355 ml), and Water (0.237 ml) to give a thin suspension. The flask was cooled in an ice-bath for 10 min, then 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.496 g, 2.52 mmol) was added in one portion, leading to a solution. The reaction was stirred for 15 minutes. 2,3,4,5,6-pentafluorophenol (0.211 ml, 2.012 mmol) was added followed by drop wise addition of triethylamine (0.351 ml, 2.52 mmol). The reaction was stirred for 30 minutes. The reaction was concentrated and purified via column chromatography (RediSep Gold 40 g, gradient elution 0-50% EtOAc:Heptane) to afford perfluorophenyl 4-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)quinazoline-7-sulfonate as a light yellow solid. (ESI) 611.2 (M+H)+.

후처리

  1. customto give a thin suspension
  2. temperatureThe flask was cooled in an ice-bath for 10 min
  3. stirringThe reaction was stirred for 30 minutes
  4. concentrationThe reaction was concentrated
  5. custompurified via column chromatography (RediSep Gold 40 g, gradient elution 0-50% EtOAc:Heptane)

출처 및 근거

ORD 기록
ord-bca14eeb282c4bcd81edc7fe47d9559d
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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