Cesium carbonate → N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

HRID 536552ノート

反応式

HRID 536552 の反応式
[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:17]2[C:21](=[O:22])[NH:20][C:19]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[N:18]2)(=[O:16])=[O:15])=[C:10]([O:30][CH3:31])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:39][CH:40]([OH:45])[C:41]([F:44])([F:43])[F:42]>CN(C)C=O.[Cl-].[NH4+]>[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:17]2[C:21](=[O:22])[N:20]([CH2:39][CH:40]([OH:45])[C:41]([F:44])([F:43])[F:42])[C:19]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)=[N:18]2)(=[O:16])=[O:15])=[C:10]([O:30][CH3:31])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2206323-Bromo-1,1,1-Trifluoro-2-PropanolHCID 135927695N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

生成物 1

HCID 46238690N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
75 °C

実験手順

An amount of 50 mg (0.108 mmol) of N-tert-butyl-4-{[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide from Example 14 and 53 mg (0.161 mmol) of caesium carbonate were suspended in 1 ml of dimethylformamide and admixed with 26 μl (0.161 mmol) of 3-bromo-1,1,1-trifluoro-2-propanol. The mixture was stirred at 75° C. for 8 hours. The suspension was diluted with saturated aqueous ammonium chloride solution. It was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. The crude product was purified by preparative HPLC [Method 5]. This gave 22 mg (36% of theory) of the target compound.

後処理

  1. extractionIt was extracted twice with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. customfreed from the solvent on a rotary evaporator
  4. customThe crude product was purified by preparative HPLC [Method 5]

出典と根拠

ORDレコード
ord-ae72c616a87d430a901e16bb54021a72
出典データセット
uspto-grants-2014_10
特許番号
US08859601B2

反応ノート

読み込み中…