Hydrochloric Acid → 6-(1H-Indol-4-yl)-4-{5-[(phenylsulfonyl)methyl]-1,3,4-oxadiazol-2-yl}-1H-indazole

HRID 38878

반응식

HRID 38878 반응식
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:16]=[C:15]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][NH:21]4)[CH:14]=[C:13]3[C:9]=2[CH:10]=[N:11][N:12]3S(C2C=CC=CC=2)(=O)=O)=[N:5][N:4]=1.O.O.[C:37]1([S:43]([O-:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[Na+].[OH-].[Na+].Cl>C(O)C.C(O)(C)C.CO.ClCCl>[NH:21]1[C:22]2[C:18](=[C:17]([C:15]3[CH:14]=[C:13]4[C:9]([CH:10]=[N:11][NH:12]4)=[C:8]([C:6]4[O:7][C:3]([CH2:2][S:43]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)(=[O:45])=[O:44])=[N:4][N:5]=4)[CH:16]=3)[CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:20]1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23681562Benzenesulfinic acid, sodium salt, dihydrateHCID 667769544-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole

생성물 1

HCID 667769046-(1H-Indol-4-yl)-4-{5-[(phenylsulfonyl)methyl]-1,3,4-oxadiazol-2-yl}-1H-indazole수율 16%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 887Methanol용매HCID 3776Isopropanol용매HCID 6344Dichloromethane용매

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온도
20 °C

실험 절차

4-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazole (60 mg, 0.110 mmol) and sodium benzenesulfinate dihydrate (33.1 mg, 0.165 mmol, available from TCI Europe) in ethanol (0.8 ml) were heated under microwave irradiation to 100° C. for 30 mins then 150° C. for 20 mins. The mixture was treated with dichloromethane (3 ml) and methanol (3 ml) and absorbed onto Florisil. This was placed on top a silica cartridge (10 g) and eluted with 0-100% ethyl acetate/cyclohexane and then 0-20% methanol/ethyl acetate. Appropriate fractions were combined and concentrated to give a yellow solid, 33 mg. The solid was treated with isopropanol (1 ml) and 2M aqueous sodium hydroxide (0.999 ml, 1.998 mmol) and stirred at 20° C. for 22 h. The mixture was neutralised with 2M aqueous hydrochloric acid, blown to dryness and purified by Mass Directed Automated Preparative HPLC. Appropriate fraction was evaporated, then azeotroped with methanol to give the title compound as a white solid (8 mg).

후처리

  1. customabsorbed onto Florisil
  2. washeluted with 0-100% ethyl acetate/cyclohexane
  3. concentrationconcentrated
  4. customto give a yellow solid, 33 mg
  5. custompurified by Mass Directed Automated Preparative HPLC
  6. customAppropriate fraction was evaporated
  7. customazeotroped with methanol

출처 및 근거

ORD 기록
ord-20985be666024876a39c0789702ab1c5
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524751B2

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