Water → Perfluorophenyl 1-(4-chloro-2-methoxyphenyl)isoquinoline-6-sulfonate

HRID 1473378노트

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HRID 1473378 반응식
C([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[O:26][CH3:27])=[N:14][CH:13]=[CH:12]2)C1C=CC=CC=1.ClN1C(C)(C)C(=[O:36])N(Cl)C1=O.[F:39][C:40]1[C:45]([F:46])=[C:44]([F:47])[C:43]([F:48])=[C:42]([F:49])[C:41]=1[OH:50].C(N(CC)CC)C.[OH2:58]>C(O)(=O)C.C(#N)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:15]2[C:16]3[C:11](=[CH:10][C:9]([S:8]([O:50][C:41]4[C:40]([F:39])=[C:45]([F:46])[C:44]([F:47])=[C:43]([F:48])[C:42]=4[F:49])(=[O:36])=[O:58])=[CH:18][CH:17]=3)[CH:12]=[CH:13][N:14]=2)=[C:20]([O:26][CH3:27])[CH:21]=1

참가 물질

8

반응물 5

HCID 962WaterHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 866874206-(Benzylthio)-1-(4-chloro-2-methoxyphenyl)isoquinoline

생성물 1

HCID 86687421Perfluorophenyl 1-(4-chloro-2-methoxyphenyl)isoquinoline-6-sulfonate수율 46.9%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매

실험 절차

A round-bottom flask was charged with 6-(benzylthio)-1-(4-chloro-2-methoxyphenyl)isoquinoline (700 mg, 1.786 mmol), acetonitrile (1.68E+04 μl), acetic acid (630 μl), and water (420 μl) to give a thin suspension. The flask was cooling in an ice-bath for 15 min, then 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (704 mg, 3.57 mmol) was added in one portion, leading to an solution. After 20 min, 2,3,4,5,6-pentafluorophenol (493 mg, 2.68 mmol) and triethylamine (1245 μl, 8.93 mmol) were added in sequence. The cooling bath was removed after a few minutes, and the mixture was warmed to room temperature. The mixture was treated with silica gel then concentrated. More silica gel was added, and the mixture was concentrated from DCM. The impregnated silica gel was eluted onto a pre-equilibrated 40-g column with 0 to 50% EtOAc/Heptane to give perfluorophenyl 1-(4-chloro-2-methoxyphenyl)isoquinoline-6-sulfonate (Intermediate NNN; 432 mg, 0.837 mmol, 46.9% yield) as a white foam. NMR and LC/MS indicated the material was about 82% pure. m/z (ESI) 516.0 (M+H)+.

후처리

  1. customto give a thin suspension
  2. temperatureThe flask was cooling in an ice-bath for 15 min
  3. customThe cooling bath was removed after a few minutes
  4. additionThe mixture was treated with silica gel
  5. concentrationthen concentrated
  6. additionMore silica gel was added
  7. concentrationthe mixture was concentrated from DCM
  8. washThe impregnated silica gel was eluted onto a pre-equilibrated 40-g column with 0 to 50% EtOAc/Heptane

출처 및 근거

ORD 기록
ord-aae422c7a05741bbbde3c5570721ad6c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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