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

HRID 38878

反応式

HRID 38878 の反応式
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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 3776Isopropanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-20985be666024876a39c0789702ab1c5
出典データセット
uspto-grants-2013_09
特許番号
US08524751B2

関連ノート

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